Potassium Carbonate → HCID 86651711, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-dimethylethyl (2-{[(5-bromo-3-thienyl)carbonyl]amino}-2-phenylethyl)carbamate (250 mg, 0.588 mmol) in dioxane/H2O (5:1, 6 mL) was added K2CO3 (325 mg, 2.35 mmol), tetrakistriphenylphosphine Pd(0) (34 mg, 29.4 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (126 mg, 0.647 mmol). The reaction mixture was heated to 80° C. in a sealed tube. After 5 h, additional tetrakistriphenylphosphine Pd(0) (34 mg, 29.4 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (126 mg, 0.647 mmol) were added. After 12 h, the reaction solution was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organics were dried (Na2SO4), concentrated under vacuum and purified on silica gel (1% MeOH in DCM) to give the title compound (250 mg, quant.) as an orange oil: LCMS (ES) m/z=427.

Provenance & Evidence