2-Amino-4-bromopyridine → tert-Butyl 7-bromo-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-bromopyridine (786 mg, 4.55 mmol) and tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate (1.39 g, 5.00 mmol) were combined in toluene (20 mL) and heated at 105° C. for 16 h. The mixture was concentrated and purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (512 mg, 32%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.93 (s, 1H), 7.46 (d, J=9.1 Hz, 1H), 7.22 (d, J=9.1 Hz, 1H), 4.69 (br s, 2H), 3.85 (br s, 2H), 2.93 (br s, 2H), 1.51 (s, 9H).

Provenance & Evidence