Stannous chloride dihydrate → HCID 58557615, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-cyclohexyl-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-amine (0.111 g, 0.268 mmol, prepared using K.1 from Example #21 Step D with 4-methylbenzene-1-sulfonyl chloride, L with cyclohexylamine) in EtOH (2.5 mL) was added tin (II) chloride dihydrate (0.060 g, 0.268 mmol). The reaction mixture was heated at about 75° C. for about 75 min. Tin (II) chloride dihydrate (0.030 g, 0.134 mmol) was added and the reaction mixture was heated at about 75° C. for about 5 h. Additional tin (II) chloride dihydrate (0.060 g, 0.268 mmol) was added and the reaction mixture was heated at about 75° C. for about 14 h. The solvent was removed under reduced pressure. The residue was diluted with EtOAc (25 mL) and washed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL). The organic portion was separated. The aqueous portion was extracted with EtOAc (3×25 mL). The organic extracts were combined, dried over MgSO4, filtered, and concd under reduced pressure to give N-4-cyclohexyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.081 g, 79%) as a brown oil: LC/MS (Table 1, Method n) Rt=0.82 min; MS m/z 385 (M+H)+.

Provenance & Evidence