Potassium Carbonate → HCID 69675426, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromobenzo[b]thiophene (702 mg, 2.07 mmol), (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (700 mg, 1.59 mmol), tetrakis(triphenylphosphine) palladium (0) (184 mg, 0.15 mmol), potassium carbonate (440 mg, 3.19 mmol) in water (2 mL) and dimethoxyethane (10 mL) was heated in a microwave reactor at 130° C. for 30 minutes. The dimethoxyethane was removed under reduced pressure. The resulting residue was partitioned between water (15 mL) and dichloromethane (15 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (20 mL). The combined organic extracts were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting residue was subjected to flash chromatography with eluant of (10% methanol in ethyl acetate) and hexane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide (S)-tert-butyl 2-(5-(4-(6-bromobenzo[b]thiophen-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (302 mg, 0.58 mmol, 36%).

Provenance & Evidence