2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 8-(cyclopropylmethoxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-8-(cyclopropylmethoxy)-7-methoxyquinolin-2(1H)-one (500 mg, 1.92 mmol), 4-bromo-3,5-dimethylpyridine (350 mg, 1.88 mmol), Pd2(dba)3 (88 mg, 0.19 mmol Pd), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (181 mg, 0.38 mmol), sodium tert-butoxide (370 mg, 3.85 mmol), and toluene (20 mL) was heated at 110° C. for 3 h under N2, and then allowed to cool to room temperature. The reaction was filtered and washed with 5% methanol in dichloromethane (500 mL×3). The filtrate was concentrated and purified by silica gel chromatography (40:1; ethyl acetate/methanol) and then reverse-phase HPLC to give 0.16 g of 8-(cyclopropylmethoxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one as white solid. MS (ESI): 366.2

Provenance & Evidence