Hydrochloric Acid → (E)-5-(1-(2-hydroxyethyl)-3-(pyridin-4-yl)-1H-pyrazol-4-yl)-2,3-dihydro-1H-inden-1-one oxime

Participants

Reaction Steps

To (E)-5-(1-(2-hydroxyethyl)-3-(pyridin-4-yl)-1H-pyrazol-4-yl)-2,3-dihydroinden-1-one O-benzyl oxime (31.9 mg; Example 4, Step 4) in 5 mL methanol was added 38 μL 6M hydrochloric acid and about 5 mg palladium hydroxide (20% by weight on carbon). A hydrogen-filled balloon was attached to the reaction vessel and the mixture was stirred at ambient temperature for 1 hour. The mixture was filtered through celite, the celite was washed with methanol, and the filtrate treated with a small amount of saturated aqueous sodium bicarbonate. The filtrate was concentrated under vacuum and the residue was purified by chromatography, eluting with a 10:1 mixture of dichloromethane-methanol to yield 13.2 mg (53% yield) of a white solid. 1H NMR (CDCl3) was consistent with the desired structure 110. LC/MS showed one peak with a M+1 molecular ion of m/z 335.4 by positive ESI.

Provenance & Evidence