Hydrochloric Acid → tert-butyl 2-[[[(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate

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Reaction Steps

(4-Methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 100) (130 mg, 0.55 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (99 mg, 0.56 mmol) were combined in ethanol (8 mL). The pH of the mixture was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the reaction mixture was refluxed for 14 h. The solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and then brine, dried over sodium sulfate, and concentrated to a solid. Purification by column chromatography (silica gel, 75 to 100% ethyl acetate in hexanes) produced tert-butyl 2-[[[(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (geometry of the oxime double bond undefined).

Provenance & Evidence