Cornforth reagent → HCID 67135814, compound

4-(2-Chloro-4-fluorophenyl)-α-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol (i.e. the product of Synthesis Example 6) (90 mg, 0.25 mmol) was dissolved in dichloromethane (8 mL), and pyridinium dichromate (113 mg, 0.3 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature for 16 h, and then the reaction mixture was partitioned between water (5 mL) and dichloromethane (5 mL). The organic phase was washed with additional water (5 mL) and with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure to give a viscous residue. This residue was purified by column chromatography through silica gel eluted with a gradient of ethyl acetate in hexane (25% to 30%) to give the title product, a compound of the present invention, as a pale yellow viscous oil (29 mg).

1. customthe reaction mixture was partitioned between water (5 mL) and dichloromethane (5 mL)
2. washThe organic phase was washed with additional water (5 mL) and with brine (5 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto give a viscous residue
6. customThis residue was purified by column chromatography through silica gel
7. washeluted with a gradient of ethyl acetate in hexane (25% to 30%)

ORD record

ord-0ab962548a99444e92ec3a37ca9d6caa

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062005B2