Facile synthesis of aryl-pyridyl, pyridazinyl, pyrazinyl, and triazinyl acetonitriles

Article abstract of DOI:10.1002/jhet.1535

Dihalo pyridine, pyrazine, and pyridazine analogues were converted to the corresponding monohalo acetonitrile analogues through nucleophilic displacement of the halogen with the anion of tert-butyl cyanoacetate. The monohalo acetonitriles reacted under Su

Full text of DOI:10.1002/jhet.1535

Month 2013
Facile Synthesis of Aryl-Pyridyl, Pyridazinyl, Pyrazinyl, and Triazinyl
Acetonitriles
A. A. Farahat1,2 and D. W. Boykin
1
*
1Department of Chemistry, Georgia State University, Atlanta, Georgia 30303
2Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
*
E-mail: dboykin@gsu.edu
Received June 28, 2011
DOI 10.1002/jhet.1535
Published online 00 Month 2013 in Wiley Online Library (wileyonlinelibrary.com).
Dihalo pyridine, pyrazine, and pyridazine analogues were converted to the corresponding monohalo
acetonitrile analogues through nucleophilic displacement of the halogen with the anion of tert-butyl
cyanoacetate. The monohalo acetonitriles reacted under Suzuki or Stille conditions to form the title compounds.
J. Heterocyclic Chem., 00, 00 (2013).
INTRODUCTION
analogues [12]. This methodology has also been applied
to monochloro pyrimidines [13]. Also preparation of 2-(6-
bromopyridin-2-yl)acetonitrile was reported through nucle-
ophilic substitution using a lithio acetonitrile reagent [14].
In this work, we extend the use of tert-butyl
cyanoacetate under moderate conditions to non-activated
2,6-dibromopyridine, 2,6-dichloropyrazine, and 3,6-
dichloropyridazine. Scheme 1 outlines our approach to the
synthesis of 6-substituted pyridyl-2-acetonitriles (5a–g).
2,6-Dibromopyridine was stirred with 1.1 equivalents of
tert-butyl cyanoacetate (2) and 2 equivalents of potassium
carbonate in dimethylformamide under nitrogen atmosphere
at 80ꢀC for 24h. Under these conditions, only one of the
bromo atoms is displaced, giving the monosubstituted
tert-butyl cyanoacetate analogue (3). The tert-butyl cyano-
acetate compounds were directly converted to the acetoni-
trile analogue (4) by heating in refluxing toluene in the
presence of a catalytic amount of p-toluene sulfonic acid.
Suzuki coupling reactions [15] between the acetonitrile (4)
and different boronic acids in the presence of 5 mol %
of Pd(PPh3)4 using a solvent mixture of toluene–methanol–
water afforded compounds (5a–f) in good yield (71–84%).
Also applying Stille coupling methodology [16] between
the acetonitrile (4) and 2-(tri-n-butyltin)furan in the presence
of 5 mol % of Pd(PPh3)4 using 1,4-dioxane as solvent
afforded compound (5g) in good yield (88%).
Compounds containing aryl/heteroaryl acetic acid and
aryl/heteroaryl ethylamine cores play important roles in the
pharmaceutical field. Compounds containing aryl/heteroaryl
acetic acid units form a large group of non-steroidal
anti-inflammatory drugs such as Indomethacin [1], Diclo-
phenac [2], Sulindac [3], Ketorolac [4], and many others.
Also, this subunit appears in a number of antifungal [5],
antiulcer [6], and anticancer compounds [7]. Aryl/heteroaryl
ethylamine containing compounds show a variety of useful
biological responses including antidiabetic [8], antiviral [9],
antipsychotic [10], and anticonvulsant activities [11].
Recently, we required a convenient synthesis of substituted
heteroaryl acetonitriles, which are important intermediates for
the synthesis of several compounds within our drug discovery
program.
We report here a facile synthesis of substituted hetero-
aryl acetonitriles, which can be readily hydrolyzed to the
corresponding acetic acids or reduced to form ethyl amine
analogues that can serve as versatile precursors for the
preparation of more complex molecules.
RESULTS AND DISCUSSION
It has been reported that tert-butyl cyanoacetate
undergoes nucleophilic displacement of nitro-activated
2-chloropyridines using boiling tetrahydrofuran in the
presence of potassium carbonate as base to yield the
corresponding tert-butyl cyanoacetate pyridine, which
can be dealkoxycarbonylated in the presence of p-toluene
sulfonic acid in boiling toluene to give the acetonitriles
Scheme 2 outlines the synthesis of 2-substituted pyrazi-
nyl-2-acetonitriles (9a–c) and 3-substituted pyridazinyl-2-
acetonitriles (9d–f). The dichloro compounds (6a and b)
were stirred with 1.1 equivalents of tert-butyl cyano-
acetate (2) and 2 equivalents of potassium carbonate in
© 2013 HeteroCorporation

A. A. Farahat and D. W. Boykin
Vol 000
Scheme 1. Reagents and conditions (a) (i) K2CO3, DMF, 80ꢀC (ii) HCl; (b) (i) p-toluene sulfonic acid, toluene, reflux (ii) Na2CO3; (c) arylboronic acid, Pd
(PPh3)4, Na2CO3, toluene, CH3OH; or tributylstannyl furan, Pd(PPh3)4, 1,4-dioxane, reflux.
CN
(a)
(b)
CN
O
CN
Br
N
O
O
Br
N
Br
N
1
Br
O
4
2
3
(c)
CN
Ar
N
5 a-g
Ar,
N
N
N
O
N
CN
OCH3
Scheme 2. Reagents and conditions (a) (i) K2CO3, DMF, (ii) HCl; (b) (i) p-toluene sulfonic acid, toluene, reflux (ii) Na2CO3; (c) arylboronic acid, Pd
(PPh3)4, Na2CO3, toluene.
CN
O
X3
X2
Y2
N
X2
X1
Y2
N
X2
X1
Y2
N
(a)
(b)
Y1
CN
O
Y1
CN
Y1
O
Cl
O
8 a,b
6 a,b
2
7 a,b
Y1 Y2 X1 X2
6a
6b
C
N
N
C
Cl
H
Nil Cl
X2
Y2
(c)
Y1
CN
X1
N
Y1 Y2 X1 X2
9 a-c
9 d-f
C
N
N
C
Ar
H
9 a-f
Nil Ar
Ar,
CN
OCH3
dimethylformamide under nitrogen atmosphere at room
temperature for 24 h. These conditions lead to selective
displacement of only one chloro atom, yielding the mono-
substituted tert-butyl cyanoacetate analogues (7a and b).
The tert-butyl cyanoacetate analogues were directly con-
verted to the acetonitrile analogues (8a–f) utilizing the
acid-catalyzed dealkoxycarbonylation method mentioned
before. Suzuki coupling [14] between the acetonitriles (8a
and b) and different boronic acids as mentioned before
afforded compounds (9a–f) in good yield (69–87%).
Scheme 3 outlines the synthesis of the phenyltriazine
acetonitrile (11) in good yield (74%) through stirring of
the methylsulfonyl triazine (10) [17] with tert-butyl cya-
noacetate (2), in the presence of potassium carbonate in
dimethylformamide under nitrogen atmosphere at room
temperature for 24 h, followed by the previously described
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Heteroaryl Acetonitriles
J= 8 Hz, 1H), 7.83 (d, J= 8 Hz, 1H), 4.46 (s, 2H); 13C NMR
(DMSO-d6): d 155.4, 154.1, 129.5, 129.0, 116.6, 23.0; ESI-HRMS:
m/z calculated for C6H4ClN3: 154.0165, found: 154.0172; Anal.
Calcd. for C6H4ClN3: C, 46.93; H, 2.63; N, 27.36. Found: C, 47.33;
H, 2.71; N, 26.99.
Scheme 3. Reagents and conditions (a) (i) K2CO3, DMF, (ii) HCl; (b) (i)
p-toluene sulfonic acid, toluene, reflux, (ii) Na2CO3.
O2
S
CN
O
(a)
(b)
N
N
CN
N
N
N
O
N
General procedure for the synthesis of 5a–f and
9a–f. Deaerated 2 M aqueous solution of Na2CO3 (5 mL) and
aryl boronic acids (5.5 mmol) in 5 mL deaerated methanol were
added to a stirred solution of the halo compounds 4, 8a and b
(5 mmol), and tetrakis(triphenylphosphine)palladium (0.288 g,
0.25 mmol) in deaerated toluene (20 mL) under a nitrogen
atmosphere. The vigorously stirred mixture was warmed to 80ꢀC
for 24 h. The solvent was evaporated under reduced pressure, the
solid was partitioned between ethyl acetate (200 mL) and 2 M
aqueous Na2CO3 (25 mL) containing 5 mL of concentrated
ammonia, to remove palladium, then washed with water, passed
through celite to remove the catalyst, dried (sodium sulfate), and
evaporated. The product was purified by column chromatography
on silica gel, using hexanes/ethyl acetate (70/30, v/v).
11
2
10
acid-catalyzed dealkoxycarbonylation using catalytic
amount of p-toluene sulfonic acid in boiling toluene.
In conclusion, we report a concise synthesis, in good
yields, of new cyanomethyl substituted heteroaryl systems,
which can be used for preparation of more complex mole-
cules for multiple applications.
EXPERIMENTAL
2-(6-phenylpyridin-2-yl)acetonitrile (5a). White solid, 0.78g
1
(81%) mp 80–80.5ꢀC; H NMR (CDCl3): d 8.16–8.14 (m, 2H),
All commercial reagents were used without purification. Melting
points were determined on a Mel-Temp 3.0 melting point apparatus
and are uncorrected. TLC analysis was carried out on silica gel
60F254 precoated aluminum sheets using UV light for detection.
1H and 13C NMR spectra were recorded on a Bruker 400 MHz
spectrometer using the indicated solvents. Mass spectra were
obtained from the Georgia State University Mass Spectrometry
Laboratory, Atlanta, GA. Elemental analysis were performed by
Atlantic Microlab Inc., Norcross, GA.
7.82–7.80 (m, 2H), 7.51–7.49 (m, 2H), 7.40 (br s,1H), 7.28 (s,
1H), 4.03 (s, 2H); 13C NMR (CDCl3): d 159.8, 156.3, 149.1,
136.9, 130.0, 127.3, 117.9, 116.3, 113.3, 113.1, 25.9; ESI-HRMS:
m/z calculated for C13H10N2: 195.0924, found: 195.0922; Anal.
Calcd. for C13H10N2: C, 80.39; H, 5.19; N, 14.42. Found: C,
80.21; H, 5.22; N, 14.39.
2-(6-(4-cyanophenyl)pyridin-2-yl)acetonitrile (5b). Yellow solid,
1
0.79 g (72%) mp 93–94ꢀC; H NMR (CDCl3): d 8.18 (d, J=8Hz,
1H), 7.90 (t, J=8Hz, 1H), 7.79–7.76 (m, 3H), 7.47 (d, J=8Hz, 1H),
7.28 (s, 1H), 4.05 (s, 2H); 13C NMR (CDCl3): d 154.3, 149.9, 141.4,
137.6, 131.7, 131.5, 126.5, 119.1, 117.7, 115.9, 111.9, 25.9; ESI-
HRMS: m/z calculated for C14H9N3: 220.0875, found: 220.0872;
Anal. Calcd. for C14H9N3: C, 76.70; H, 4.14; N, 19.17. Found: C,
76.72; H, 4.24; N, 19.19.
General procedure for the synthesis of 3 and 7a and b. A
mixture of the dihalo compound 1, 6a and b (60 mmol), tert-butyl
cyanoacetate (2) (9.5mL, 66mmol), and K2CO3 (16.56 g,
120 mmol) in anhydrous DMF (25 mL) was stirred at room
temperature under nitrogen atmosphere for 24 h (in the case of 3,
starting material disappeared after heating at 80ꢀC for 24h) . The
mixture was diluted with ice, acidified with concentrated HCl to
pH 1, and extracted with ethyl acetate. The organic layer was
separated, washed with water, dried (sodium sulfate), and
evaporated. These compounds were used directly in the next step.
2-(6-(4-methoxyphenyl)pyridin-2-yl)acetonitrile (5c). White solid,
0.88 g (79%) mp 79–79.5ꢀC; 1H NMR (CDCl3): d 8.01 (d, J=8Hz,
2H), 7.78–7.75 (m, 1H), 7.66 (t, J= 8 Hz, 1H), 7.32–7.28 (m, 1H),
7.03–7.01 (m, 2H), 4.02 (s, 2H), 3.91 (s, 3H); 13C NMR (CDCl3): d
159.9, 156.3, 149.2, 136.7, 130.1, 127.3, 127.2, 117.9, 116.2, 113.3,
55.3, 25.9; ESI-HRMS: m/z calculated for C14H12N2O: 225.1028,
found: 225.1030; Anal. Calcd. for C14H12N2O: C, 74.98; H, 5.39; N,
12.49. Found: C, 74.97; H, 5.36; N, 12.44.
General procedure for the synthesis of
4 and 8a
and b. Compounds 3 and 7a and b were dissolved in toluene
(100 mL), and p-toluene sulfonic acid monohydrate (0.5 g) was
added. The mixture was heated under reflux for 12 h, cooled to
room temperature, the toluene was decanted, and the black residue
was extracted with ethyl acetate (2 Â 50 mL). The combined
organic phases were washed with aqueous NaHCO3 solution
(50 mL), dried (sodium sulfate), and evaporated under reduced
pressure. The product was purified by column chromatography on
silica gel, using hexanes/ethyl acetate (70/30, v/v) as eluent.
2-(2,3′-bipyridin-6-yl)acetonitrile (5d). Yellow solid, 0.78 g
1
(81%) mp 92–92.3ꢀC; H NMR (DMSO-d6): d 9.26 (s, 1H), 8.64
(br s, 1H), 8.42 (d, J= 8 Hz, 1H), 7.99–7.95 (m, 2H), 7.53–7.50 (m,
1H), 7.44 (d, J= 8 Hz, 1H), 4.29 (s, 2H); 13C NMR (DMSO-d6):
d 153.1, 150.9, 149.5, 147.5, 138.2, 133.4, 132.9, 123.3, 121.5,
119.0, 117.7, 25.4; ESI-HRMS: m/z calculated for C12H9N3:
196.0875, found: 196.0867; Anal. Calcd. for C12H9N3: C, 73.83; H,
4.65; N, 21.52. Found: C, 73.81; H, 4.69; N, 21.49.
2-(6-bromopyridin-2-yl)acetonitrile (4). Yellow solid, 8.44 g
(71%, 2 steps) mp 46–46.5ꢀC (reported 43–43.5ꢀC) [14a]; 1H NMR
(CDCl3): d 7.64–7.6 (m, 1H), 7.49–7.46 (m, 2H), 3.95 (s, 2H); 13
NMR (CDCl3): d 150.6, 141.1, 138.7, 126.8, 120.1, 115.3, 25.2.
C
2-(2,4′-bipyridin-6-yl)acetonitrile (5e). Yellow solid, 0.81 g
1
(84%) mp 98–99ꢀC; H NMR (DMSO-d6): d 8.72–8.71 (m, 2H),
2-(6-chloropyrazin-2-yl)acetonitrile (8a). White solid, 6 g
(65%; 2 steps) mp 41–43ꢀC; 1H NMR (CDCl3): d 8.61 (s, 1H), 8.58
(s, 1H), 3.97 (s, 2H); 13C NMR (CDCl3): d 148.0, 145.1, 143.8,
140.2, 114.3, 22.9; ESI-HRMS: m/z calculated for C6H4ClN3:
154.0166, found: 154.0172; Anal. Calcd. for C6H4ClN3: C, 46.93;
H, 2.63; N, 27.36. Found: C, 46.94; H, 2.61; N, 27.09.
8.09–8.07 (m, 3H), 8.02 (t, J =8Hz, 1H), 7.52 (d, J=8Hz, 1H),
4.32 (s, 2H); 13C NMR (DMSO-d6): d 153.0, 151.0, 149.1, 138.0,
133.8, 132.1, 123.3, 121.3, 117.7, 25.3; ESI-HRMS: m/z
calculated for C12H9N3: 196.0875, found: 196.0870; Anal. Calcd.
for C12H9N3: C, 73.83; H, 4.65; N, 21.52. Found: C, 73.87; H,
4.75; N, 21.30.
2-(6-chloropyridazin-3-yl)acetonitrile (8b). White solid, 5.59 g
2-(6-(pyrimidin-5-yl)pyridin-2-yl)acetonitrile (5f). Orange
1
(61%, 2 steps) mp 59–59.5ꢀC; H NMR (DMSO-d6): d 7.98 (d,
solid, 0.69 g (71%) mp 103–103.5ꢀC; 1H NMR (DMSO-d6):
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A. A. Farahat and D. W. Boykin
Vol 000
d 9.44–9.43 (m, 2H), 9.26 (br s, 1H), 8.10 (d, J= 8 Hz, 1H), 8.02
(d, J= 8 Hz, 1H), 7.51 (d, J= 8 Hz, 1H), 4.31 (s, 2H); 13C NMR
(DMSO-d6): d 158.0, 154.3, 151.3, 150.6, 138.5, 130.6, 122.3,
119.5, 117.6, 25.3; ESI-HRMS: m/z calculated for C11H8N4:
197.0872, found: 197.0830; Anal. Calcd. for C11H8N4: C, 67.34;
H, 4.11; N, 28.55. Found: C, 67.06; H, 4.22; N, 28.49.
2H); 13C NMR (DMSO-d6): d 156.0, 153.6, 139.3, 132.5,
131.0, 127.2, 127.0, 125.3, 116.9, 112.1, 23.3; ESI-HRMS: m/z
calculated for C13H8N4: 221.0827, found: 221.0827; Anal.
Calcd. for C13H8N4: C, 70.90; H, 3.66; N, 25.44. Found: C,
71.02; H, 3.81; N, 25.22.
2-(6-(4-methoxyphenyl)pyridazin-3-yl)acetonitrile (9f). White
solid, 0.85 g (78%) mp 69–71ꢀC; 1H NMR (DMSO-d6): d 8.75 (d,
J= 8 Hz, 2H), 7.90 (br s, 2H), 6.90 (d, J = 8 Hz, 2H), 4.40 (s, 2H),
3.70 (s, 3H); 13C NMR (DMSO-d6): d 155.0, 151.2, 144.3, 140.1,
138.7, 127.5, 126.2, 114.2, 113.6, 54.3, 23.5; ESI-HRMS: m/z
calculated for C13H11N3O: 226.0980, found: 226.0970; Anal.
Calcd. for C13H11N3O: C, 69.32; H, 4.92; N, 18.66. Found: C,
69.31; H, 4.96; N, 18.48.
Synthesis of 2-(6-(furan-2-yl)pyridin-2-yl)acetonitrile
(5g). Tetrakis(triphenylphosphine)palladium (0.25 mmol, 0.29 g)
was added to
a stirred mixture of 4 (1 g, 5 mmol) and
2-(tributylstannyl)furan (1.87 g, 5.25 mmol) in deaerated dry
dioxane (15 mL) under nitrogen atmosphere. The vigorously
stirred mixture was warmed to 90ꢀC for 24 h. The solvent was
removed under reduced pressure, the solid was partitioned
between ethyl acetate (200mL) and concentrated ammonia (5 mL)
to remove palladium, washed with water, passed through celite to
remove the catalyst, dried (sodium sulfate), and evaporated. The
product was purified by column chromatography on silica gel,
using hexanes/ethyl acetate (80/20, v/v) as eluent.
Yellow solid, 0.8 g (88%) mp 89–90ꢀC; 1H NMR (CDCl3):
d 7.76 (dd, J = 8 Hz, 2 Hz, 1H), 7.64 (d, J = 8 Hz, 1H), 7.54 (br
s, 1H), 7.30 (d, J = 8 Hz, 1H), 7.09 (br s, 1H), 6.54 (s, 1H), 4.01
(s, 2H); 13C NMR (CDCl3): d 149.4, 148.6, 142.8, 137.0, 119.1,
117.7, 116.6, 116.1, 111.2, 108.6, 25.7; ESI-HRMS: m/z calcu-
lated for C11H8N2O: 185.0715, found: 185.0719; Anal. Calcd. for
C11H8N2O: C, 71.73; H, 4.38; N, 15.21. Found: C, 71.45; H,
4.43; N, 14.96.
Synthesis of 2-(5-phenyl-1,2,4-triazin-3-yl)acetonitrile (11). A
mixture of 3-(methylsulfonyl)-5-phenyl-1,2,4-triazine (10) [17]
(2.35 g, 10 mmol), tert-butyl cyanoacetate (1.6 mL, 11 mmol),
and K2CO3 (2.76 g, 20 mmol) in anhydrous DMF (15 mL) was
stirred at room temperature under nitrogen atmosphere for 24 h.
The mixture was diluted with ice, acidified with concentrated
HCl to pH 1, and extracted with ethyl acetate. The organic layer
was separated, washed with water, dried (sodium sulfate), and
evaporated. The residue was dissolved in toluene (20 mL), and
p-toluene sulfonic acid monohydrate (0.1 g) was added. The
mixture was heated under reflux for 12 h, cooled to room
temperature, and the toluene was decanted and the black residue
was extracted with ethyl acetate (2 Â 20 mL). The combined
organic phases were washed with aqueous NaHCO3 solution
(20 mL), dried (sodium sulfate), and evaporated under reduced
pressure. The product was purified by column chromatography
on silica gel, using hexanes/ethyl acetate (65/35, v/v) as eluent.
2-(6-phenylpyrazin-2-yl)acetonitrile (9a). White solid, 0.84 g
1
(87%) mp 71–73ꢀC; H NMR (CDCl3): d 9.04 (br s, 1H), 8.63
(br s, 1H), 8.07 (br s, 2H), 7.54–7.53 (m, 3H), 4.03 (s, 2H); 13C
NMR (CDCl3): d 151.3, 144.6, 140.2, 140.1, 134.3, 129.5,
128.2, 126.9, 115, 23.5; ESI-HRMS: m/z calculated for
C12H9N3: 194.0724, found: 194.0718; Anal. Calcd. for
C12H9N3: C, 73.83; H, 4.65; N, 21.52. Found: C, 73.72; H,
4.67; N, 21.51.
1
Yellow solid, 1.33 g (74%, 2 steps) mp 120–121ꢀC; H NMR
(DMSO-d6): d 10.1 (s, 1H), 8.37 (br s, 2H), 7.70–7.65 (m, 3H),
4.69 (s, 2H); 13C NMR (DMSO-d6): d 159.9, 155.0, 144.3,
132.4, 128.5, 128.2, 127.2, 114.6, 25.9; ESI-HRMS: m/z calcu-
lated for C11H8N4: 197.0827, found: 197.0833; Anal. Calcd. for
C11H8N4: C, 67.34; H, 4.11; N, 28.55. Found: C, 67.73; H,
4.01; N, 28.31.
2-(6-(4-cyanophenyl)pyrazin-2-yl)acetonitrile (9b). White
1
solid, 0.86 g (79%) mp 88–88.5ꢀC; H NMR (CDCl3): d 9.15
(br s, 1H), 8.73 (br s, 1H), 8.29 (m, 2H), 7.85 (m, 2H), 4.08
(s, 2H); 13C NMR (CDCl3): d 149.1, 145.0, 141.7, 140.6,
140.4, 138.4, 132.0, 126.7, 117.3, 114.6, 23.5; ESI-MS: m/z
calculated for C13H8N4: 221.0827, found: 221.0818; Anal.
Calcd. for C13H8N4: C, 70.90; H, 3.66; N, 25.44. Found: C,
70.88; H, 3.69; N, 25.33.
Acknowledgment. This work was supported by an award from
the Bill and Melinda Gates Foundation.
2-(6-(4-methoxyphenyl)pyrazin-2-yl)acetonitrile (9c). Yellow
solid, 1 g (86%) mp 79–79.4ꢀC; 1H NMR (CDCl3): d 8.97
(s, 1H), 8.54 (s, 1H), 8.05 (d, J = 8 Hz, 2H), 7.06 (d, J = 8 Hz,
2H), 4.01 (s, 2H), 3.90 (s, 3H); 13C NMR (CDCl3): d 160.6,
151.0, 144.3, 139.7, 139.3, 127.5, 126.8, 115.0, 113.6, 54.5,
23.5; ESI-HRMS: m/z calculated for C13H11N3O: 226.0980,
found: 226.0972; Anal. Calcd. for C13H11N3O: C, 69.32; H,
4.92; N, 18.66. Found: C, 69.23; H, 4.99; N, 18.67.
2-(6-phenylpyridazin-3-yl)acetonitrile (9d). Yellow solid,
0.72 g (74%) mp 69–69.5ꢀC; 1H NMR (DMSO-d6): d 8.29
(d, J = 8 Hz, 1H), 8.17–8.15 (m, 2H), 7.82 (d, J = 8 Hz, 1H),
7.59–7.57 (m, 3H), 4.49 (s, 2H); 13C NMR (DMSO-d6): d
157.4, 152.9, 135.0, 129.7, 128.6, 126.8, 126.4, 124.5, 117.0,
23.2; ESI-HRMS: m/z calculated for C12H9N3: 196.0875, found:
196.0878; Anal. Calcd. for C12H9N3: C, 73.83; H, 4.65; N,
21.52. Found: C, 74.10; H, 4.59; N, 21.39.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Heteroaryl Acetonitriles
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