1-Butanol → 5-(1-Methyl-3-pyridin-4-yl-1H-pyrazol-4-yl)-2,3-dihydroinden-1-one oxime

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Reaction Steps

To 5-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-4-yl)-2,3-dihydroinden-1-one O-benzyl oxime (2.50 g; Example 3, Step 4) in 60 mL methanol was added 0.89 g palladium hydroxide (20% by weight on carbon) and 6.3 mL 6M hydrochloric acid. A hydrogen-filled balloon was attached to the reaction vessel and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was filtered through celite and the celite was washed with methanol. The filtrate was concentrated under vacuum and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate was washed with brine and evaporated to yield 1.0 g of crude product as a white solid. The aqueous layer was reextracted with two portions of n-butanol. The n-butanol was evaporated under vacuum to afford an additional 0.4 g crude product as a white solid. The solids were combined and washed with two 15 mL portions of water, dissolved in a 1:1 mixture of dichloromethane-methanol, filtered, and the filtrate evaporated under vacuum. The residue was triturated with ethyl acetate and dried to afford 0.98 g (51% yield) of product as a white solid. 1H NMR (CDCl3) was consistent with the desired structure 113. LC/MS showed a peak with a M+1 molecular ion of m/z 305.4 by positive ESI.

Provenance & Evidence