Cesium carbonate → 1-(2-Cyanophenyl)-5-furyl-3-trifluoromethylpyrazole

HRID 649827Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]1[NH:19][NH:18][C:17]([C:21]([F:24])([F:23])[F:22])(O)[CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:19]1[C:15]([C:11]2[O:10][CH:14]=[CH:13][CH:12]=2)=[CH:16][C:17]([C:21]([F:24])([F:22])[F:23])=[N:18]1)#[N:5]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-fluorobenzonitrile (0.605 g, 5 mmol) and 5-furyl-3-trifluoromethyl-3-hydroxypyrazoline (1.1 g, 5 mmol) in DMF (10 mL) was added Cs2CO3 (1.63 g, 5 mmol), and the resulting mixture was stirred at 110° C. for 16 hours. The mixture was diluted with EtOAc, washed with brine (×5), dried over MgSO4, and purified by column chromatography with a gradient solvent (hexane to ethyl acetate) to give 1-(2-cyanophenyl)-5-furyl-3-trifluoromethylpyrazole and 1-(2-cyanophenyl)-3-furyl-5-trifluoromethylpyrazole (1.27 g, 83.8%) in a ratio of 95 to 5. 1H NMR (CDCl3) δ7.82 (dd, J=7.7 Hz, J=1.5 Hz, 1H), 7.77 (dd, J=7.7 Hz, J=1.5 Hz, 1H), 7.66 (td, J=7.7 Hz, J=1.1 Hz, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.39 (d, J=1.4 Hz, 1H), 6.96 (s, 1H), 6.37 (dd, J=3.3 Hz, J=1.4 Hz, 1H), 6.04 (d, J=3.3 Hz, 1H); 19F NMR (CDCl3): δ−62.98; ESMS(+): 304 (M+H, 100).

Workup

washwashed with brine (×5)
dry with materialdried over MgSO4
custompurified by column chromatography with a gradient solvent (hexane to ethyl acetate)

Sources & evidence

ORD record: ord-649695367b324791a972a5b6fdd359f2
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271237B1

Reaction notes

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