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 record

ord-36f3003132ad417188ce992498687998

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969587B2