Potassium Carbonate → 2-chloro-4'-[2-(2,6-dichloro-phenyl)-5-isopropyl-2H-pyrazol-3-ylmethoxy]-biphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Into a 8 mL flask was added 256 mg (0.56 mmol) of 2-[5-(4-bromo-phenoxymethyl)-1 (2,6-dichloro-phenyl)-1H-pyrazol-3-yl]-propan-2-ol, 134 mg (0.67 mmol) of (4-carboxy-2-chlorophenyl)boronic acid, 200 mg of potassium carbonate (1.68 mmol), 10 mg (0.017 mmol) of dicyclohexyl palladium acetate and 2 mL of ethanol. The reaction mixture was heated to 80° C. for 4 h. After cooling, the crude reaction mixture was filtered through a pad of celite, concentrated in vacuo, and purified on a reverse phase HPLC-MS to afford 2-chloro-4′-[2-(2,6-dichloro-phenyl)-5-isopropyl-2H-pyrazol-3-ylmethoxy]-biphenyl-4-carboxylic acid as an off white solid (34 mg, 11%); 1H NMR (400 MHz, CDCl3): δ 8.16 (m, 1H), 7.98 (d, J=8.1 Hz, 1H), 7.45 (d, J=7.83 Hz, 2H) 7.35 (m, 4H), 6.88 (d, J=8.84 Hz, 2H), 6.54 (s, 1H), 4.92 (s, 2H), 1.66 (s 6H), MS (ES): 531 [M+H]+.

Provenance & Evidence