Potassium Carbonate → 4-[(1,3-Dimethyl-1H-pyrazol-5-yl)oxy]-3,5-difluorobenzonitrile

HRID 2174622Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[C:12](=[O:13])[CH2:11][C:10]([CH3:14])=[N:9]1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:25])[C:23]=1F)[C:19]#[N:20]>CN(C)C=O>[CH3:7][N:8]1[C:12]([O:13][C:23]2[C:16]([F:15])=[CH:17][C:18]([C:19]#[N:20])=[CH:21][C:22]=2[F:25])=[CH:11][C:10]([CH3:14])=[N:9]1

Participants

Conditions

Temperature: 75 °C

Procedure

Potassium carbonate (1.38 g, 10 mmol) was added to a solution of 2,4-dihydro-2,5-dimethyl-3H-pyrazol-3-one (0.70 g, 6.3 mmol) in N,N-dimethylformamide (15 mL). 3,4,5-Trifluorobenzonitrile (0.94 g, 6.0 mmol) was added, and the reaction mixture was heated at 75° C. under a nitrogen atmosphere for 16 h, then allowed to cool. The reaction mixture was partitioned between water (60 mL) and ethyl acetate (30 mL). The organic phase was washed with water (2×30 mL) and brine (30 mL), dried over MgSO4, and concentrated to give the title compound as a yellow oil (1.38 g).

Workup

temperatureto cool
customThe reaction mixture was partitioned between water (60 mL) and ethyl acetate (30 mL)
washThe organic phase was washed with water (2×30 mL) and brine (30 mL)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-8317200baf0c434b81eade0702d75a70
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062005B2

Reaction notes

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