3-Nitrophenylboronic Acid → HCID 71075495, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-nitrophenyl)boronic acid (188 mg, 1.13 mmol), ethyl 1-(5-bromo-1,3-thiazol-2-yl)piperidine-4-carboxylate (300 mg, 0.94 mmol), palladium(II) acetate (10.5 mg, 0.047 mmol), and tris(2-methylphenyl)phosphane (286 mg, 0.94 mmol) in 1,2-dimethoxyethane (1.9 mL) and 2M aqueous sodium carbonate (0.7 mL, 1.4 mmol) was heated to 100° C. in the microwave for 30 minutes. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL) and washed with 1:1 water:brine (50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by CombiFlash (0-40% ethyl acetate/hexanes) provided 79 mg (0.22 mmol, 23% yield) of ethyl 1-[5-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate as a yellow solid.

Provenance & Evidence