Chloride → HCID 24966727, compound

Participants

Reaction Conditions

Reaction Steps

Into a 100-ml RBF under argon were charged with tert-butyl 4-(6-bromo-2-oxo-3,4-dihydroquinazolin-1(2H)-yl)piperidine-1-carboxylate (0.50 g, 1 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.6 g, 2 mmol), tetrakis(triphenylphosphine)palladium (0.07 g, 0.06 mmol), EtOH (1.00 ml, 17 mmol), and ethylene-glycol dimethyl ether (5.00 ml, 48 mmol), followed by sodium carbonate (2 ml, 4 mmol). The reaction was stirred at 90° C. for 20 h. LC-MS indicated mainly the desired product and none of the starting chloride. The reaction was cooled, diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4). Flash chromatography with 25:10:65, 40:10:50, 50:10:40, 60:10:30, 70:10:20, and 80:10:10 EtOAc-CH2Cl2-Hexane of the concentrated organic layers gave tert-butyl 4-(6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-2-oxo-3,4-dihydroquinazolin-1(2H)-yl)piperidine-1-carboxylate as a white amorphous solid. MS m/e 527.2 (M+H+Na)+.

Provenance & Evidence