Dichloromethane → 4-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)cinnoline-3-carboxylic acid

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 mg, 0.282 mmol) and methyl 4-chlorocinnoline-3-carboxylate (94.0 mg, 0.422 mmol) was treated with PdCl2dppf.CH2Cl2 (20.6 mg, 0.028 mmol) in the presence of 1,8-Diazabicycloundec-7-ene (DBU, 300.0 mg, 1.971 mmol, 7.0 equiv) in DMSO (1 mL) and water (1 mL). The reaction mixture was heated at 110° C. for 12 min in oil bath. The reaction mixture was purified by HPLC to give 4-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)cinnoline-3-carboxylic acid.

Provenance & Evidence