Methanol → Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)piperazine-1-carboxylate

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Reaction Conditions

Reaction Steps

Into a 50 mL round bottom flask purged and maintained with an inert atmosphere of nitrogen was placed tert-butyl 4-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate (400 mg, 0.90 mmol). To this was added NaOH (90 mg, 2.25 mmol). Addition of methanol (20 mL) was next. To the mixture was added H2O (8 mL). The resulting solution was allowed to react, with stirring, for 4 hours while the temperature was maintained at 90° C. in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. A filtration was performed and the filter cake was washed with H2O. This resulted in 180 mg (66%) of tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperazine-1-carboxylate as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.96 (m, 4H), 3.56 (m, 4H), 6.73 (s, 1H), 6.97 (d, 1H), 7.88 (d, 1H), 8.22 (d, 1H), 8.97 (s, 1H). m/z 303 (M++1).

Provenance & Evidence