Stannous chloride dihydrate → N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (0.15 g, 0.57 mmol) in EtOH (10 mL) was added tin (II) chloride dihydrate (0.65 g, 2.9 mmol). The reaction mixture was heated at about 55° C. for about 1 h. The solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL) were added. The solid that formed was collected by vacuum filtration, washed with EtOAc (25 mL), and discarded. The filtrate was washed with saturated aqueous NaHCO3 (3×20 mL), dried over anhydrous MgSO4, filtered, and concd to give N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.107 g, 87%) as a brown residue: LC/MS (Table 1, Method c) Rt=1.21 min; MS m/z 231 (M+H)+.

Provenance & Evidence