Potassium Carbonate → HCID 68156487, compound

HRID 537475Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[F:14][C:15]([F:22])([F:21])[C:16]1[CH:17]=[N:18][NH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:11][CH:10]([CH3:12])[CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([N:18]2[CH:17]=[C:16]([C:15]([F:22])([F:21])[F:14])[CH:20]=[N:19]2)=[CH:3][CH:4]=1)=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(6-chloropyridin-3-yl)-3-methylbutan-1-one (1.0 g, 5.1 mmol) and 4-(trifluoromethyl)-1H-pyrazole (766 mg, 5.62 mmol) in anhydrous DMF (20 mL) was added potassium carbonate (2.12 g, 15.3 mmol). The mixture was stirred at 50° C. for 6 h. The reaction mixture was poured into brine (30 mL) and extracted with ethyl acetate (30 mL*2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography to give 3-methyl-1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-one (1.4 g) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.92 (d, J=2.0 Hz, 1H), 8.85 (s, 1H), 8.33 (dd, J=2.0, 8.4 Hz, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.88 (s, 1H), 2.79 (d, J=6.8 Hz, 2H), 2.31-2.21 (m, 1H), 0.96 (d, J=6.8 Hz, 6H).

Workup

extractionextracted with ethyl acetate (30 mL*2)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-e5b430655d384a88ace83282ccc76eca
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859591B2

Reaction notes

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