Methanol → HCID 178483068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-bromo-N-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexylmethyl}-2-trifluoromethoxy-benzenesulfonamide obtained in step H of example 1 (122 mg, 0.198 mmol) in toluene (2.7 mL) were added MeOH (0.9 mL), 2 M aqueous K2CO3 (0.9 mL), phenylboronic acid (29.0 mg, 0.237 mmol), and tetrakis(triphenylphosphine)palladium (23.0 mg, 0.02 mmol). The reaction mixture was stirred at 130° C. for 10 hr. The mixture was poured into water, and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography H-silica gel, 25% EtOAc in hexane and silica gel, 9% MeOH in CHCl3) to give trans-3-trifluoromethoxy-biphenyl-4-sulfonic acid {4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexylmethyl}-amide (77 mg, 0.125 mmol) as a white solid.

Provenance & Evidence