Nitrogen → HCID 67527663, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-3-yl]-acetic acid ethyl ester (267 mg, 0.770 mmol) and 5-(4-bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (280 mg, 0.616 mmol) in toluene (10 mL) is evacuated and refilled with N2 three times. Pd(OAc)2 (5.5 mg, 0.024 mmol), 2-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (20 mg, 0.049 mmol), and potassium phosphate, tribasic, N-hydrate (262 mg, 1.23 mmol) are added. The mixture is stirred at 100° C. for 15 hours. The reaction mixture is cooled to room temperature and filtered through a pad of celite. The filtrate is concentrated, and the residue is purified by flash chromatography (eluted with 25% EtOAc/Hexanes) and the appropriate fractions are concentrated. The material is dried in vacuo to afford (6-{4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (43 mg, 12% yield). ES/MS m/e 592.8; 594.8 (M+1).

Provenance & Evidence