Potassium Carbonate → 1,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

Participants

Reaction Steps

1,1-dimethylethyl [2-({[5-bromo-2-(3-furanyl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (140 mg, 0.277 mmol), 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (54 mg, 0.277 mmol), Pd(PPh3)4 (16 mg, 13.8 μmol) and K2CO3 (153 mg, 1.11 mmol) in dioxane (2.3 mL) and H2O (462 uL) were combined in a sealed tube. After 4 h at 80° C., additional 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (54 mg, 0.277 mmol) and Pd(PPh3)4 (16 mg, 13.8 μmol) were added. After an additional 12 h, the reaction contents were partitioned between H2O/DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly: LCMS (ES) m/z=507 (M+H)+.

Provenance & Evidence