Dimethylformamide → 1-(3-methyl-4-nitrobenzyl)-4-pentafluoropropyl-3-trifluoromethyl-1H-pyrazole

HRID 2243253Notes

Reaction equation

I[C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH3:17])[CH:9]=2)[CH:6]=1.[F:22][C:23]([F:32])([F:31])[C:24](F)(F)[C:25]([F:28])([F:27])I.CN(C=O)C>C(OCC)(=O)C.[Cu]>[CH3:17][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[CH2:7][N:5]1[CH:6]=[C:2]([C:25]([F:28])([F:27])[CH2:24][C:23]([F:32])([F:31])[F:22])[C:3]([C:18]([F:21])([F:20])[F:19])=[N:4]1

Participants

Conditions

Temperature: 132.5 °C

Procedure

4-Iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazole (2.06 g), copper powder (0.95 g), heptafluoro-1-iodopropane (2.96 g) and DMF (14 ml) were set in an autoclave and heated and stirred for 8 hours, maintaining the inside temperature of 130-135° C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 ml) and an insoluble matter was filtered with Celite and washed with ethyl acetate. The filtrate was concentrated under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrobenzyl)-4-pentafluoropropyl-3-trifluoromethyl-1H-pyrazole (0.80 g).

Workup

temperatureheated
temperatureAfter cooling to room temperature
filtrationan insoluble matter was filtered with Celite
washwashed with ethyl acetate
concentrationThe filtrate was concentrated under the reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-288bac1d412b4fc9afe4441875b1fa9c
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674807B2

Reaction notes

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