4-(2-methyl-1H-imidazol-1-yl)aniline → 4-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one

Participants

Reaction Conditions

Reaction Steps

8-chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (173 mg, 0.60 mmol), 4-(2-methyl-1H-imidazol-1-yl)aniline (125 mg, 0.72 mmol), PdOAc2 (13.47 mg, 0.06 mmol), biphenyl-2-yldicyclohexylphosphine (21.03 mg, 0.06 mmol) and cesium carbonate (489 mg, 1.50 mmol) were placed in a microwave vial equipped with a stirring bar. The vial was capped, DME (4 mL) was added, the vial was flushed with nitrogen via a syringe and the mixture was heated to 100°C in a microwave reactor for 1 h. The residue was diluted with CH2Cl2 and filtered through a short plug of Celite. The filtrate was evaporated and the residue was purified by ISCO column chromatography on silica (gradient elution 0-6% methanol in dichloromethane) to give 4-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (105 mg, 41.1 %). 68 mg given to Per Svensson crystallography.

Provenance & Evidence