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

Temperature

0 °C

To a stirred solution of 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylethanol (290 mg, 0.87 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (0.7 mL, 3.5 mmol) in anhydrous dichloromethane (5 mL) was added titanium(IV) tetrachloride (1M solution in toluene, 1.9 mL, 1.9 mmol) dropwise at 0° C. under argon. The reaction mixture was stirred at 0° C. for 30 min and rt for 2 hr before being quenched by the slow addition of saturated aqueous sodium bicarbonate solution (15 mL). The mixture was filtered through a pad of celite that was then washed with dichloromethane (10 mL). The aqueous filtrate was reextracted with dichloromethane (10 mL). The combined dichloromethane layers were dried (Na2SO4), concentrated and purified by silica gel flash chromatography to give methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-4-phenylbutanoate (216 mg, 0.52 mmol, 60% yield) as an oil.

1. custombefore being quenched by the slow addition of saturated aqueous sodium bicarbonate solution (15 mL)
2. filtrationThe mixture was filtered through a pad of celite that
3. washwas then washed with dichloromethane (10 mL)
4. dry with materialThe combined dichloromethane layers were dried (Na2SO4)
5. concentrationconcentrated
6. custompurified by silica gel flash chromatography

ORD record

ord-814d2b335d3e432e88562cf8833acbca

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067447B2