methyl 1H-1,2,4-triazole-3-carboxylate → 1-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

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Reaction Steps

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and methyl 1H-1,2,4-triazole-5-carboxylate. The two isomers were separated by silica gel chromatography eluted with 20% acetone to flash out the less polar spot and 50% acetone to flash out the second spot (more polar spot). Compound 10: m/e+ 362 for C20H20N5O2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 7.95 (s, 2H), 7.65 (d, J=8.0 Hz, 2H), 7.56 (d, J=9.1 Hz, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.10 (dd, J=1.4, 9.1 Hz, 1H), 6.15 (s, 2H), 3.98 (s, 3H), 2.38 (s, 3H), 2.31 (s, 3H) ppm; Compound 11: m/e+ 362 for C20H20N5O2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.74 (s, 1H), 7.58 (d, J=9.5 Hz, 1H), 7.54 (d, J=7.7 Hz, 2H), 7.24 (d, J=7.7 Hz, 2H), 7.14 (d, J=9.5 Hz, 1H), 5.81 (s, 2H), 3.98 (s, 3H), 2.37 (s, 3H), 2.29 (s, 3H) ppm.

Provenance & Evidence