3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the above 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal in acetone (3 mL) was added Jones' reagent (1 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 30 min before being concentrated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate solution and 10% aqueous citric acid solution, and then extracted with ethyl acetate (3×10 mL). The combined ethyl acetate extracts were dried (Na2SO4), concentrated and purified by reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA) to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanoic acid (100 mg, 0.32 mmol, 43% yield for 2 steps) as a yellow oil.

Provenance & Evidence