Water → 1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

HRID 1750449Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]([NH2:19])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]#[N:19])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazole-4-carboxamide (500 mg, 1.91 mmol) in DMF (4 mL) was added cyanuric chloride (0.267 mL, 1.91 mmol) at 0° C., and the mixture was stirred at 0° C. for 14 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→50% ethyl acetate/hexane) to give 1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (430 mg, 1.77 mmol, 92%) as a white powder.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customdried
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a80c1ecc3f6040d0bb52459d99c939a2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156837B2

Reaction notes

Loading…