Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2-dimethylpropanoate

Participants

Reaction Steps

To solution of 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde (1.0 g, 4.16 mmol) and 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.85 mL, 4.2 mmol) in 10 mL of dry DCM at 0° C. was added TiCl4 (0.8 mL of 1.0 M DCM solution, 0.8 mmol) The reaction was stirred 2 h and then quenched with aqueous sodium bicarbonate and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography eluting with 1:2 EtOAc/hexane to give 700 mg (50% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2-dimethylpropanoate. MS found: (M+H)+=343.

Provenance & Evidence