Potassium Carbonate → phenyl 3-cyclobutyl-1-phenyl-1H-pyrazol-5-ylcarbamate

To a stirred mixture of 3-cyclobutyl-1-phenyl-1H-pyrazol-5-amine (1.00 g, 4.69 mmol) and potassium carbonate (1.48 g, 10.68 mmol) in THF (50 mL) at −5° C., was added phenyl chloroformate (0.88 g, 5.62 mmol) dropwise. After stirring for a further 30 min at −5° C., the reaction mixture was warmed to rt and stirred for a further 15 h. The mixture was quenched with water and extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate, concentrated under reduced pressure, and dried under vacuum to afford an oil. Recrystallization from petroleum ether gave phenyl 3-cyclobutyl-1-phenyl-1H-pyrazol-5-ylcarbamate (1.30 g, 83%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 6.53-7.53 (m, 12H), 3.57 (m, 1H), 2.26-2.38 (m, 4H), 1.64-2.07 (m, 2H); LC-MS (ESI) m/z 334 (M+H)+.

1. temperaturethe reaction mixture was warmed to rt
2. stirringstirred for a further 15 h
3. customThe mixture was quenched with water
4. extractionextracted with dichloromethane
5. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customdried under vacuum
8. customto afford an oil
9. customRecrystallization from petroleum ether

ORD 기록

ord-2c9ab59fce8e4820ab74e03a47db98bf

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08618289B2