2-Bromopyridine → HCID 67336561, compound

Participants

Reaction Conditions

Reaction Steps

Add tris(dibenzylideneacetone)dipalladium(0) (52 mg, 0.06 mmol), DPPP (47 mg, 0.11 mmol), sodium tert-butoxide (26 mg, 0.27 mmol) and 2-bromopyridine (23 μl, 0.23 mmol) to a solution of 6-aminomethyl-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (60 mg, 0.19 mmol) in anhydrous toluene (3 mL). Degas the slurry under house vacuum, then flush with nitrogen. Stir the mixture at 95° C. for 20 h. Cool the mixture to room temperature, dilute with diethyl ether (20 mL) and filter through Celite®. Concentrate the filtrate in vacuo to obtain crude 3-tert-butoxycarbonyl-7-chloro-6-(pyridin-2-ylaminomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg). Continue processing with the crude mixture. MS (ES+) m/z: 388.2 (M+H)+.

Provenance & Evidence