Water → 7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid dimethylamide

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Reaction Steps

1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (50 mg, 0.177 mmol) was dissolved in N,N-dimethylformamide and the flask was purged with carbon monoxide. Dimethylamine (0.32 ml of a 5.5M ethanol solution) was added followed by palladium bis(diphenylphosphino)ferrocene dichloride, dichloromethane complex (14 mg, 0.0177 mmol). A carbon monoxide-filled balloon was attached and the flask was stirred in a 100 C bath for 48 hrs. The reaction was worked up by addition of water and ethyl acetate. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined ethyl acetate layers were washed with water and then saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated to a residue. The residue was purified by silica gel chromatography (methanol/dichloromethane) to give 16 mg (32%) of product. MP=98-101 C, (M+H)+=275.

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