反应详情

A mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (200 mg, 90 mmol) and tert-butyl[2-(aminooxy)ethyl]methylcarbamate (Reference Example 14) (180 mg, 94 mmol) in EtOH (20 mL) was adjusted to pH 4-5 with HCl (1.2 mL of a 1 N HCl solution in diethyl ether, 1.2 mmol). The reaction mixture was heated to reflux. After 15.5 h, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (25 mL) and washed with saturated NaHCO3 (2×10 mL). The combined organic layers were washed with saturated NaCl (10 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 99:1 CH2Cl2/MeOH to 95:5 CH2Cl2/MeOH) gave tert-butyl methyl[2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethyl]carbamate (geometry of the oxime double bond undefined).

1. temperatureThe reaction mixture was heated to reflux
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additionThe residue was diluted with EtOAc (25 mL)
4. washwashed with saturated NaHCO3 (2×10 mL)
5. washThe combined organic layers were washed with saturated NaCl (10 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customPurification by column chromatography (silica gel, 99:1 CH2Cl2/MeOH to 95:5 CH2Cl2/MeOH)