(Z)-(1-(benzyloxy)prop-1-enyloxy)trimethylsilane → 4-(3-(benzyloxy)-1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-methyl-3-oxopropyl)benzoic acid

Participants

Reaction Steps

To a solution of 4-((1-(4-fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzoic acid (180 mg, 0.5 mmol) and (Z)-(1-(benzyloxy)prop-1-enyloxy)trimethylsilane (10.0 mmol, 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 3 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated. MPLC purification on SiO2 using a 0-100% EtOAc/hexane gradient gave 140 mg (55% yield) of 4-(3-(benzyloxy)-1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-methyl-3-oxopropyl)benzoic acid. MS found: (M+H)+=509.

Provenance & Evidence