G
H. Jiang et al.
Paper
Synthesis
1H NMR (400 MHz, CDCl3): = 8.15 (d, J = 6.8 Hz, 1 H), 7.67 (d, J = 8.2
Hz, 1 H), 7.60 (d, J = 7.6 Hz, 1 H), 7.43 (t, J = 7.8 Hz, 1 H), 7.23 (t, J = 8.0
Hz, 1 H), 7.09 (t, J = 7.4 Hz, 1 H), 7.04 (d, J = 8.4 Hz, 1 H), 6.90 (t, J = 6.8
Hz, 1 H), 3.88 (s, 3 H).
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2011, 54, 2455. (b) Sanger, D. J. Behav. Pharmacol. 1995, 6, 116.
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2018, 13, 2009. (c) Dharmana, T.; Swapna, M. Pharma Chem.
2017, 9,11 35. (d) Jadhav, S. A.; Shioorkar, M. G.; Chavan, O. S.;
Sarkate, A. P.; Shinde, D. B. Synth. Commun. 2017, 47, 285.
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2018, 1665. (b) Marhadour, S.; Bazin, M.-A.; Marchand, P. Tetra-
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5972.
13C NMR (101 MHz, CDCl3): = 157.09, 145.19, 141.77, 131.88,
130.05, 124.51, 123.81, 121.89, 120.45, 117.67, 112.84, 111.05, 94.69,
55.45.
HRMS (ESI): m/z calcd for C14H12BrN2O [M + H]+: 303.0128; found:
303.0141.
3-Bromo-2-(3-chlorophenyl)imidazo[1,2-a]pyridine (4l)
Yield: 46.14 mg (75%); gray solid; mp 118 °C.
1H NMR (400 MHz, CDCl3): = 8.19–8.15 (m, 2 H), 8.05–8.02 (m, 1 H),
7.63 (d, J = 8.2 Hz, 1 H), 7.42 (d, J = 8.0 Hz, 1 H), 7.39–7.34 (m, 1 H),
7.31–7.26 (m, 1 H), 6.96 (dt, J = 6.8, 0.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): = 145.49, 141.25, 134.70, 134.54,
129.69, 128.32, 127.87, 125.89, 125.43, 124.03, 117.77, 113.31, 92.08.
HRMS (ESI): m/z calcd for C13H9BrClN2 [M + H]+: 306.9632; found:
306.9645.
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(b) Liu, P.; Shen, Z.; Yuan, Y.; Sun, P. Org. Biomol. Chem. 2016, 14,
6523. (c) Pérez, V. M.; Fregoso-López, D.; Miranda, L. D. Tetrahe-
dron Lett. 2017, 58, 1326. (d) Mondal, S.; Samanta, S.; Santra, S.;
Bagdi, A. K.; Hajra, A. Adv. Synth. Catal. 2016, 358, 3633. (e) Lu,
S.; Zhu, X.; Li, K.; Guo, Y.-J.; Wang, M.-D.; Zhao, X.-M.; Hao, X.-
Q.; Song, M.-P. J. Org. Chem. 2016, 81, 8370.
Methyl 3-(2-Phenylimidazo[1,2-a]pyridin-3-yl)propanoate (5)
Yield: 33.64 mg (60%); brown solid; mp 134–136 °C.
1H NMR (400 MHz, CDCl3): = 8.03 (d, J = 8.8 Hz, 1 H), 7.78–7.76 (m, 2
H), 7.64 (d, J = 8.2 Hz, 1 H), 7.46 (t, J = 7.8 Hz, 2 H), 7.35 (t, J = 8.2 Hz, 1
H), 7.20–7.16 (m, 1 H), 6.84 (td, J = 6.8, 1.2 Hz, 1 H), 3.65 (s, 3 H), 3.47
(m, 2 H), 2.70–2.66 (m, 2 H).
13C NMR (101 MHz, CDCl3): = 172.63, 144.54, 142.70, 132.42,
128.56, 128.04, 127.60, 123.94, 122.89, 118.36, 117.62, 112.26, 51.86,
32.07, 19.19.
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Funding Information
We thank the Hunan Province Science Foundation for Youths
(2018JJ3215), the Scientific Research Foundation of Hunan Provincial
Education Department (18C0147), Hunan Agricultural University
Science Foundation for High-Level Personnel and Double First-Class
Construction Project of Hunan Agricultural University (SYL2019064),
the Basic Research Foundation of China Tobacco Yunnan Industrial
Corporation (2018JC04) and the Applied Basic Research Foundation of
Yunnan Province (2017FD236).
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© 2020. Thieme. All rights reserved. Synthesis 2020, 52, A–H