Sodium borohydride → methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-hydroxy-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate

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Reaction Steps

To a solution of methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate (i.e. the product of Example 10) (100 mg, 0.24 mmol) in methanol (10 mL) was added sodium borohydride (19 mg, 0.48 mmol) and the reaction mixture was stirred at ambient temperature for 1 hour. After TLC analysis (30% ethyl acetate/pet ether) showed completion of reaction, the solvent was concentrated under vacuum. The crude residue was cooled to 0° C. and acidified with 1N HCl. The aqueous mixture was extracted three times with ethyl acetate. The combined the organic phases were washed with water, brine and dried over Na2SO4. The solvent was concentrated under vacuum to give the title compound, a compound of the present invention, (60 mg, 60% yield) as a solid.

Provenance & Evidence