Potassium Carbonate → HCID 58256467, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with a stir bar and 2-amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (750 mg, 2.401 mmol) and 4-bromobenzaldehyde (444 mg, 2.401 mmol), Pd2(dba)3 (220 mg, 0.240 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (572 mg, 1.201 mmol), and potassium carbonate (365 mg, 2.64 mmol). The tube was evacuated and backfilled with argon three times. Fully degassed tert-amyl alcohol (8 mL) was added to the mixture via syringe. The solution was sealed and stirred overnight in an oil bath at 100° C. The following day, the reaction was allowed to cool to room temperature and taken up in ethyl acetate. The suspension was washed in aqueous sodium bicarbonate twice and brine twice, and the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification was performed via silica gel chromatography (0-3% methanol in ethyl acetate).

Provenance & Evidence