Molecules 2019, 24, 4177
7 of 12
1
1
-Phenyl-1H-pyrrole (3b) [31]: white solid (0.38 g, 94%). m.p. 60–62 C. H-NMR (400 MHz, CDCl ) δ
3
(
ppm): 7.43–7.37 (4H, m), 7.25–7.21 (1H, m), 7.08 (2H, t, J = 2.2 Hz), 6.34 (2H, t, J = 2.2 Hz). MS (ESI)
+
m/z: 144.04 [M + H] .
◦
1
3
-(1H-Pyrazol-1-yl)benzaldehyde (3c) [32]: off white solid (0.46 g, 95%), m.p. 28–30 C. H-NMR (400 MHz,
CDCl3)
δ
(ppm): 10.08 (1H, s), 8.19 (1H, t, J = 1.8 Hz), 8.05–8.02 (2H, m), 7.81–7.76 (2H, m), 7.64 (1H, t,
+
J = 7.9 Hz), 6.52 (1H, t, J = 2.1 Hz). MS (ESI) m/z: 173.08 [M + H] .
◦
1
2
-(1H-Pyrazol-1-yl)benzoic acid (3d) [33]: white solid (0.51 g, 96%), m.p. 128–129 C. H-NMR (400 MHz,
CDCl3)
δ
(ppm): 11.40 (1H, br), 8.05–8.02 (1H, dd, J = 7.8 Hz, 1.2 Hz), 7.76–7.74 (2H, m), 7.62–7.58 (1H,
+
m), 7.49–7.40 (2H, m), 6.48 (1H, s). MS (ESI) m/z: 189.06 [M + H] .
2
-(1H-Pyrazol-1-yl)aniline (3e) [34]: brown oil (0.38 g, 85%). 1H-NMR (400 MHz, CDCl3)
δ (ppm):
7
.74–7.71 (2H, m), 7.19–7.13 (2H, m), 6.85–6.76 (2H, m), 6.44 (1H, t, J = 2.0 Hz), 4.63 (2H, br). MS (ESI)
+
m/z: 160.09 [M + H] .
1
1
-(4-(1H-Pyrazol-1-yl)phenyl)ethan-1-one (3f) [35]: yellow oil (0.47 g, 90%). H-NMR (400 MHz, CDCl )
3
δ
(ppm): 8.08–8.06 (2H, m), 8.02 (1H, d, J = 2.5 Hz), 7.83–7.81 (2H, m), 7.78 (1H, d, J = 1.4 Hz), 6.53 (1H,
+
t, J = 2.0 Hz), 2.63 (3H, s). MS (ESI) m/z: 187.09 [M + H] .
1
Ethyl 3-(1H-pyrazol-1-yl)benzoate (3g) [36]: yellow liquid (0.55 g, 91%). H-NMR (400 MHz, CDCl )
δ
3
(
(
ppm): 8.31 (1H, t, J = 1.8 Hz), 7.99 (1H, d, J = 2.4 Hz), 7.97–7.93 (2H, m), 7.74 (1H, d, J = 1.6 Hz), 7.53
1H, t, J = 8.0 Hz), 6.49 (1H, t, J = 2.0 Hz), 4.44–4.38 (2H, q, J = 14.3 Hz, 7.2 Hz), 1.41 (3H, t, J = 7.1 Hz).
+
MS (ESI) m/z: 217.10 [M + H] .
◦
1
Methyl 4-(1H-pyrazol-1-yl)benzoate (3h) [37]: white solid (0.53 g, 93%), m.p. 103–105 C. H-NMR
(
=
400 MHz, CDCl3)
δ
(ppm): 8.15–8.12 (2H, m), 8.00 (1H, d, J = 2.4 Hz), 7.80–7.77 (2H, m), 7.76 (1H, d, J
+
1.4 Hz), 6.51 (1H, t, J = 2.1 Hz), 3.93 (3H, s). MS (ESI) m/z: 203.11 [M + H] .
1
2
-(1H-Pyrazol-1-yl)benzonitrile (3i) [38]: yellow oil (0.47 g, 98%). H-NMR (400 MHz, CDCl )
δ
(ppm):
3
8
2
.15 (1H, d, J = 2.5 Hz), 7.81–7.79 (3H, m), 7.77 (1H, d, J = 1.3 Hz), 7.72–7.68 (1H, m), 6.55 (1H, t, J =
.1 Hz). MS (ESI) m/z: 170.07 [M + H] .
+
1
2
8
6
-(1H-Pyrrol-1-yl)pyridine (3j) [39]: colorless oil (0.34 g, 84%). H-NMR (400 MHz, CDCl )
δ (ppm):
3
.43–8.42 (1H, m), 7.75–7.71 (1H, m), 7.52 (2H, t, J = 2.3 Hz), 7.32 (1H, d, J = 8.3 Hz), 7.11–7.08 (1H, m),
+
.36 (2H, t, J = 2.3 Hz). MS (ESI) m/z: 145.04 [M + H] .
◦
1
2
-(1H-Imidazol-1-yl)pyridine (3k) [40]: white solid (0.36 g, 88%), m.p. 40–41 C. H-NMR (400 MHz,
CDCl3)
δ
(ppm): 8.50–8.48 (1H, m), 8.35 (1H, s), 7.85–7.80 (1H, m), 7.65 (1H, t, J = 1.3 Hz), 7.37–7.35
+
(1H, m), 7.27–7.23 (1H, m), 7.20 (1H, s). MS (ESI) m/z: 146.08 [M + H] .
1
2
-(2-Methyl-1H-imidazol-1-yl)pyridine (3l) [41]: colorless oil (0.38 g, 85%). H-NMR (400 MHz, CDCl ) δ
3
(
1
ppm): 8.56–8.54 (1H, m), 7.86–7.82 (1H, m), 7.32–7.29 (2H, m), 7.28 (1H, d, J = 1.5 Hz), 7.02 (1H, d, J =
.5 Hz), 7.02 (1H, d, J = 1.4 Hz), 2.59 (3H, s). MS (ESI) m/z: 160.09 [M + H] .
+
◦
1
2
-(1H-Imidazol-1-yl)pyrimidine (3m) [42]: white solid (0.34 g, 83%), m.p. 120–122 C. H-NMR (400 MHz,
(ppm): 8.71 (2H, d, J = 4.8 Hz), 8.64 (1H, s), 7.90 (1H, s), 7.21 (1H, t, J = 4.8 Hz), 7.18 (1H, s).
CDCl3)
δ
+
MS (ESI) m/z: 147.06 [M + H] .
◦
1
2
-(2-Methyl-1H-imidazol-1-yl)pyrimidine (3n) [43]: white solid (0.36 g, 80%), m.p. 90–92 C. H-NMR
(
(
400 MHz, CDCl3)
1H, d, J = 1.3 Hz), 2.82 (3H, s). MS (ESI) m/z: 161.10 [M + H] .
δ
(ppm): 8.72 (2H, d, J = 4.8 Hz), 7.86 (1H, d, J = 1.4 Hz), 7.18 (1H, t, J = 4.8 Hz), 6.97
+
1
2
-(Piperidin-1-yl)pyridine (4a) [44]: colorless oil (0.40 g, 87%). H-NMR (400 MHz, CDCl ) δ (ppm):
3
8
.16–8.15 (1H, m), 7.44–7.39 (1H, m), 6.63 (1H, d, J = 8.6 Hz), 6.54–6.51 (1H, m), 3.52 (4H, d, J = 4.9 Hz),
+
1
.62 (6H, s). MS (ESI) m/z: 163.13 [M + H] .