Diethyl Ether → tert-Butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Participants

Reaction Steps

A slurry of tert-butyl 6-amino-2-chloro-4,5-dimethylnicotinate (1.2 g, 4.7 mmol, 1 equiv) and 1-bromo-3-(2-bromo-1,1-dimethoxyethyl)benzene (2.3 g, 7.0 mmol, 1.5 equiv) in chlorobenzene (23 mL) was heated at reflux for 1.5 h. Upon cooling to ambient temperature, the reaction was added slowly to ether. The slurry was stirred for 15 min and the filtered to provide the product as a HBr salt (1.86 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 8.73 (s, 1H), 8.32 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.47-7.40 (m, 1H), 2.56 (s, 3H), 2.30 (s, 3H), 1.60 (s, 9H); LCMS (ESI, M+1): 435.05.

Provenance & Evidence