Ammonium Chloride → (3-Bromo-6-ethoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl)-carbamic acid tert-butyl ester

温度

-78 °C

To a THF (150 mL) solution of (6-ethoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl)-carbamic acid tert-butyl ester (16.5 g, 61.4 mmol), was added a 2.77M n-hexane solution of n-butyllithium (15.9 mL, 44 mmol) while stirring at −78° C. The mixture was stirred at −78° C. for one hour, and then 1,2-dibromotetrafluoroethane (2.61 mL, 22 mmol) was added, and the mixture was stirred while heating to room temperature for three hours. A saturated aqueous solution of ammonium chloride was added and acetic acid was added, and the mixture was extracted with ethyl acetate and washed with brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate: 0% then 30%) to obtain 4.95 g (13.7 mmol) of the title compound.

1. stirringThe mixture was stirred at −78° C. for one hour
2. stirringthe mixture was stirred
3. temperaturewhile heating to room temperature for three hours
4. extractionthe mixture was extracted with ethyl acetate
5. washwashed with brine
6. dry with materialdried over magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

ORDレコード

ord-c2d2587d7b5144dd95599b8e24411f34

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530504B2