Hydrochloric Acid → 1-(1-Allyl-5-hydroxymethyl-1H-pyrrol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

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Reaction Steps

To a chilled (0° C.) solution of 250 mg (0.51 mmol) 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl ester in anhydrous CH2Cl2 was added 1.5 mL (1.5 mmol) of a 1 M solution of diisobutylaluminum hydride (DIBAL) in CH2Cl2. The reaction was warmed to reflux and stirred overnight. The reaction was cooled to room temperature, poured into 100 mL of 1N aqueous HCl, then made basic with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by HPLC using CH3CN—H2O buffered with 0.1% TFA (5-90% gradient). The fractions from the column were concentrated in vacuo to remove CH3CN and then the resulting aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate. The solvent was concentrated in vacuo to afford 8.0 mg (4%) of the title compound. MS m/z 446.41 (MH+).

Provenance & Evidence