(1-Methoxy-2-phenylvinyloxy)trimethylsilane → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoate

Participants

Reaction Steps

To a solution of (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (318 mg, 1.0 mmol) and (1-methoxy-2-phenylvinyloxy)trimethylsilane (3 mmol) which was prepared using General Silyl Ketene Acetal Method A in 10 mL of dry DCM was added TiCl4 (1.0 mL of 1.0 M DCM solution, 1.0 mmol) and then stirred 1 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated and purified on SiO2 by MPLC using a EtOAc/hexane gradient to give 376 mg (84% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoate. MS found: (M+H)+=451.

Provenance & Evidence