N,N-Dimethylcyclohexylamine → 4-ethenyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazolyl-3,5-bis(trifluoromethyl)benzene

HRID 895689Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(N(C)C)CCCCC1.[CH3:25][C:26]([N:28]([CH3:30])C)=O.CN1[C:36]([CH3:37])=[CH:35][C:34]([C:38]([F:41])([F:40])[F:39])=[N:33]1>C1(C)C=CC=CC=1.O>[CH:36]([C:35]1[CH:34]([C:38]([F:41])([F:40])[F:39])[N:33]([C:5]2[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)[N:28]([CH3:30])[C:26]=1[CH3:25])=[CH2:37]

Participants

Conditions

Temperature: 110 °C

Procedure

10 g of 3,5-bis(trifluoromethyl)bromobenzene are mixed with 11 ml of cyclohexyldimethylamine and 30 ml of dimethylacetamide and degassed. 38 mg of palladium acetate and 152 mg of di(tert-butyl)phenylphosphine are dissolved in 5 ml of dimethylacetamide and added to the mixture. The mixture is transferred to an autoclave and 30 bar of ethylene are injected. The mixture is then heated to 110° C. and stirred at this temperature for 3 hours. At the end of the reaction, the mixture is cooled and the pressure released. Subsequently, 8.3 g of 1,5-dimethyl-3-trifluoromethyl-1H-pyrazole are added to the reaction mixture and the mixture is heated to 130° C. for 12 h. Afterwards, the mixture is cooled, added to water and worked up with toluene. Yield over the two steps: 10.5 g (76%) of slightly brownish solid.

Workup

customdegassed
dissolution38 mg of palladium acetate and 152 mg of di(tert-butyl)phenylphosphine are dissolved in 5 ml of dimethylacetamide
additionadded to the mixture
customAt the end of the reaction
temperaturethe mixture is cooled
temperaturethe mixture is heated to 130° C. for 12 h
temperatureAfterwards, the mixture is cooled
customYield over the two steps

Sources & evidence

ORD record: ord-518d4053520f46878639b40f802f9319
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916839B2

Reaction notes

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