Methanol → 2-[3-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethylamine dihydrochloride

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Reaction Conditions

Reaction Steps

A solution of 2-{2-[3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione (4.54 g, 10.5 mmol) in dioxane is treated with anhydrous hydrazine (8.3 mL, 265 mmol), heated at 50° C. for 3 h, concentrated in vacuo, diluted with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a clear gum residue. Chromatography (1:9 methanol:CH2Cl2) of the residue affords the free amine of the title compound as a clear gum. The free amine is dissolved in ethanol, acidified with 2N aqueous HCl and concentration in vacuo. Crystallization of the resultant residue from ethanol/ether affords the title compound as a white solid, 3.20 g, mp 195-197° C., characterized by mass spectral and HNMR analyses.

Provenance & Evidence