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 200 mg (0.454 mmol) of 5-(4-bromophenoxymethyl)-1-(2,6-dichlorophenyl)-3-isopropyl-1H-pyrazole, 108 mg (0.54 mmol) of (4-carboxy-2-chlorophenyl)boronic acid, 186 mg of potassium carbonate (1.36 mmol) and 2 mL of 9:1 DME-water. The solution was sparged under argon and 6.5 mg (0.01 mmol) of palladium dppf was added. The reaction mixture was heated to 80° C. for 4 h. After cooling, the crude reaction was filtered through a pad of celite, concentrated in vacuo, and purified directly on a reverse phase HPLC-MS to afford 2-chloro-4′-[2-(2,6-dichlorophenyl)-5-isopropyl-2H-pyrazol-3-ylmethoxy]-biphenyl-4-carboxylic acid as an off white solid, yield (80.1 mg, 34%); 1H NMR (400 MHz, DMSO-d6): δ 13.37 (s, 1H), 8.04 (m, 1H), 7.96 (dd, J=8.1 (1.77) Hz, 1H), 7.73 (d J=8.1 Hz, 2H) 7.61 (m, 1H), 7.55 (d, J=7.83 Hz, 1H), 7.41 (d, J=8.84 Hz, 2H), 6.98 (d, J=9.09 Hz, 2H), 6.61 (s, 1H), 5.01 (s, 1H), 4.83 (s, 2H), 3.02 (m 1H), 2.52 (s, 1H), 1.31 (d J=6.82 Hz 6H), MS (ES): 515 [M+H]+.

Provenance & Evidence