Ammonium Chloride → tert-butyl N-(3-bromo-6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate

A tetrahydrofuran (40 mL) solution of tert-butyl(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (1.20 g, 4.74 mmol) was cooled to −78° C., and n-butyllithium (1.57 M, 6.64 mL, 10.4 mmol) was added dropwise thereto, and the mixture was stirred for 30 minutes. Then, 1,2-dibromotetrafluoroethane (619 μl, 5.21 mmol) was added to the mixture, and the reaction mixture was warmed to room temperature, and stirred at room temperature for one hour. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, and a substance of interest was extracted with ethyl acetate. The organic layer was washed with brine and 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: 50% then 66%) to obtain 1.39 g (4.32 mmol) of the title compound.

1. stirringstirred at room temperature for one hour
2. extractiona substance of interest was extracted with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

ORDレコード

ord-c649c0deb82342c1a33eb64dc231f13d

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530504B2