4-Bromopyridinium chloride → HCID 69272331, compound

Participants

Reaction Conditions

Reaction Steps

Bubble nitrogen through benzyl-(2,3-dihydro-1H-indol-7-ylmethyl)carbamic acid tert-butyl ester (3.7 g, 10.9 mmol) in 1,4-dioxane (50 mL) in a sealed tube. Mix with 4-bromopyridine hydrochloride (4.3 g, 21.9 mmol), palladium diacetate (0.5 g, 2.18 mmol), 2-(dicyclohexylphosphino)biphenyl (0.76 g, 2.18 mmol) and sodium tert-butoxide (3.1 g, 32.7 mmol). Stir the mixture 110° C. for 16 hours. Cool and filter, then concentrate the filtrate. Purify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1) to isolate a solid as the title compound (1.5 g, 33%). MS (ESI) m/z 416 (M+H)+.

Provenance & Evidence