1-Ethynyl-3-methoxybenzene → HCID 53690642, compound

Participants

Reaction Steps

2.0 g (5 mmol) (S)-8-chloro-11,12,13,13a-tetrahydro-1-iodo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was heated to boiling under reflux for 9 hours with 0.73 g (5.6 mmol) of 3-methoxyphenylacetylene, 65 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 65 mg of copper(I) iodide in 20 ml of diethylamine and 20 ml of N,N-dimethylformamide. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with methylene chloride/methanol (99:1). By crystallization from methylene chloride and ethyl acetate there was obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-[(m-methoxyphenyl)ethynyl]-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 204°-205°.

Provenance & Evidence