Potassium Permanganate → HCID 24957618, compound

Participants

Reaction Steps

To a chilled (0° C.) solution of 0.3 g (0.5 mmol) 1-(1-allyl-6-bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol in acetone-H2O (3:1) was added 93.2 mg (0.6 mmol) of KMnO4 in 5 mL of a 3:1 mixture of acetone-H2O dropwise. After 2 hours, the reaction was filtered and the solvent was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvent was concentrated in vacuo. The residue was purified by HPLC (5-100% CH3CN-water buffered with TFA). The material from the column was concentrated, in vacuo to remove the acetonitrile. The aqueous layer was made basic and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 60 mg (23%) of the title compound. MS m/z 579.35 (MH+).

Provenance & Evidence