Diethyl Ether → HCID 66706896, compound

Participants

Reaction Steps

To a stirred solution of 1.0 M neopentyl magnesium chloride in diethyl ether (50 mL, 50 mmol) at −78° C. under nitrogen, add via syringe a solution of 0.5 M zinc chloride in THF (100 mL, 50 mmol). Warm gradually to ambient temperature and transfer via syringe of this solution (25 mL, ˜8.33 mmol) to a stirred solution of 3-tert-butoxycarbonyl-6-(5-bromo-pyridin-2-ylmethylthio)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (300 mg, 0.62 mmol) in THF (2 mL) at ambient temperature. Add dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (50 mg, 0.061 mmol) and heat at 65° C. for 6 h. Cool to ambient temperature, dilute with EtOAc, wash with water, dry over anhydrous MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (6:1) to give 3-tert-butoxycarbonyl-7-chloro-6-[5-(2,2-dimethyl-propyl)-pyridin-2-ylmethylthio]-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (69 mg, 24%). MS (APCI+) m/z: 501 (M+H)+. Use a method similar to the General Procedure 1-4 to give the title compound as a white powder. MS (APCI+) m/z: 375 (M+H)+.

Provenance & Evidence