alpha-Bromo-o-chlorotoluene → N-[(2-Chlorophenyl)methyl]-N-[4-(5H-pyrrolo(2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl)-4-morpholineacetamide

Participants

Reaction Steps

A mixture of 0.11 g of N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamide, 56 mg of O-chlorobenzyl bromide and 0.41 g of K2 CO3 in 5 ml of acetonitrile is heated at reflux for 18 hours. An additional 30 mg of O-chlorobenzyl bromide and 0.4 mmol of sodium hydride is added followed by heating for 24 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried with Na2SO4 and evaporated to give 0.18 g of a residue which is purified by chromatography on silica gel with 1:1 ethyl acetate-methylene chloride to give 80 mg of off white solid. MS(CI): 555(M+H).

Provenance & Evidence