Dichloromethane → 4-(8-chloro-6-methylquinolin-5-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(3,5-Dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (100.0, 0.282 mmol) and 5-bromo-8-chloro-6-methylquinoline (72.2 mg, 0.282 mmol) was treated with PdCl2dppf.CH2Cl2 (20.9 mg, 0.028 mmol) in the presence of 1,8-Diazabicycloundec-7-ene (DBU, 204.0 mg, 1.34 mmol, 4.76 equiv) in DMSO (0.2 mL) and water (0.2 mL). The reaction mixture was heated at 120° C. in oil bath. The reaction mixture was diluted with THF (3 mL) and purified by Gilson preparative HPLC to give 4-(8-chloro-6-methylquinolin-5-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Provenance & Evidence