Sodium Thiosulfate → methyl 4-(5-bromo-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

Temperature

80 °C

N-bromosuccinimide (391 mg) was added to an N,N-dimethylformamide (3.6 ml) solution of the methyl 4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate (200 mg) obtained in (Example 1.3) <Step 1>, and the obtained mixture was then stirred in a nitrogen atmosphere at 80° C. for 40 minutes. Thereafter, N-bromosuccinimide (391 mg) was further added to the reaction solution, and the obtained mixture was then stirred in a nitrogen atmosphere at 80° C. for 15 hours. Thereafter, a sodium thiosulfate aqueous solution (40 ml) and a saturated sodium hydrogen carbonate aqueous solution (60 ml) were successively added to the reaction solution, and the reaction mixture was then extracted with ethyl acetate (60 ml) twice. Organic layers were gathered. The gathered organic layer was washed with a saturated saline (100 ml) three times, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then dried under reduced pressure, so as to obtain the title compound (274 mg) in the form of a brown solid.

1. customobtained in (Example 1.3) <Step 1>
2. stirringthe obtained mixture was then stirred in a nitrogen atmosphere at 80° C. for 15 hours
3. extractionthe reaction mixture was then extracted with ethyl acetate (60 ml) twice
4. washThe gathered organic layer was washed with a saturated saline (100 ml) three times
5. dry with materialwas then dried over anhydrous sodium sulfate
6. distillationThe solvent was distilled away under reduced pressure
7. customthe obtained residue was then dried under reduced pressure

ORD record

ord-5772f52b6c6f41c9b9b1390e3228fc0d

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440970B2