5-Methyl-3-phenylisoxazole-4-carboxylic acid → 4-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 406 mg (2 mmol) 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (commercially available) and 4 mL SOCl2 was heated to reflux for 3 h. After evaporation of all volatiles the residue was added to a mixture of 206 mg (2 mmol) 1H-pyrrole-2-carboxylic acid methyl ester (commercially available) and 440 mg (3 mmol) AMCl3 in 25 mL dichloroethane and heated to reflux for 3 h. After cooling to room temperature the precipitate was collected and washed with dichloromethane. The residue was purified on silica eluting with a gradient of ethyl acetate and heptane affording 210 mg (37%) of the title compound as white foam. (m/e): 311.0 (MH+; 100%).

Provenance & Evidence