Ethanol → HCID 68857594, compound

Participants

Reaction Conditions

Reaction Steps

Combine 6-bromomethyl-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (700 mg, 1.89 mmol), pyridine-3-boronic acid (273 mg, 2.22 mmol), tetrakis(triphenylphospine)palladium(0) (1.1 g, 0.95 mmol), and sodium carbonate (600 mg, 5.66 mmol) in a mixture of toluene (14 mL), ethanol (3.5 mL) and water (0.7 mL). Heat the mixture to 60° C. for 12 h under nitrogen. Cool the reaction and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane and hexane/EtOAc (10:1, 5:1 and 1:1) to obtain 3-tert-butoxycarbonyl-7-chloro-6-pyridin-3-ylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an off-white solid (410 mg, 59%).

Provenance & Evidence