Sodium methanolate methanol → 4-(4-Fluoro-benzyl)-1-hydroxy-3-oxo-6-trifluoromethyl-3,4-dihydro-4,4a-diaza-fluorene-2-carboxylic acid methyl ester

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A mixture of 1-[(2-ethoxycarbonyl-acetyl)-(4-fluoro-benzyl)-amino]-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (160 mg, 0.32 mmol) in 0.5 N NaOMe/MeOH solution (2.5 mL, 1.25 mmol) was refluxed overnight. After cooled, the mixture was concentrated, and the residue was dissolved in water (80 mL), acidified to pH=3-4 using 1 N HCl solution, extracted with EtOAc (2 times). Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Crude product was purified by silica gel chromatography (50%-100% EtOAc/DCM then 2%-10% MeOH/DCM) to provide the title compound 31 mg. ESI (m/z): 435.14 (M+H)+.

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