Nitrogen → 6-{4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-2-methyl-benzofuran-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran-3-carboxylic acid methyl ester (162 mg, 0.512 mmol) and 5-(4-bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (256 mg, 0.563 mmol) in toluene (5 mL) is evacuated and refilled with N2 three times. Pd(OAc)2 (11.5 mg, 0.051 mmol), 2-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (42 mg, 0.102 mmol), and potassium phosphate (tribasic, N-hydrate, 218 mg, 1.02 mmol) in 0.5 mL of water are added. The resulting mixture is evacuated and refilled with N2 three times. The mixture is stirred at 110° C. for 16 hours and cooled to room temperature. The mixture is filtered through a pad of celite, and the filtrate is concentrated. The residue is purified by silica gel chromatography with 25% EtOAc/Hexanes to provide the product 6-{4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-2-methyl-benzofuran-3-carboxylic acid methyl ester (89 mg, 31%). ES/MS m/e 564.8 (M+1).

Provenance & Evidence