N-bromobutanimide → HCID 66614279, compound

To a mixture of 5-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole (i.e. the product of Step B) (1.53 g, 7.3 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added portionwise N-bromosuccinimide (1.37 g, 7.7 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was diluted with ice water (20 mL) and saturated aqueous sodium bisulfite solution (15 mL), briefly stirred, and then partitioned between water (75 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by MPLC (10 to 40% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a solid (1.84 g).

1. additionAfter the addition
2. stirringbriefly stirred
3. custompartitioned between water (75 mL) and ethyl acetate (100 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe resulting material was purified by MPLC (10 to 40% gradient of ethyl acetate in hexanes as eluant)

ORD record

ord-e87162726b874a87b4350f144982331e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131693B2