Water → HCID 67344043, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one (prepared as in Example 111) (152.3 mg, 0.2515 mmol) in ethanol (3 mL) was added ammonium chloride (59.0 mg, 1.10 mmol), iron powder (70.4 mg, 1.26 mmol), and water (5 mL). The reaction mixture was stirred at 70° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered through celite to remove iron and inorganic solids, rinsing with ethanol. The filtrate was neutralized with saturated aqueous sodium bicarbonate, and extracted twice with dichloromethane. The combined organic extracts were dried over magnesium sulphate, filtered, and evaporated in vacuo to yield 134.5 mg (93%) of 6-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one, which was carried forward without purification. LCMS (Method E, ESI): RT=1.43 min, m+H=576.2.

Provenance & Evidence