Hydrochloric Acid → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzene

HRID 1293154Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:10]([F:13])([F:12])[F:11])=[N:5][N:6]([CH3:9])[C:7]=1[CH3:8])#[CH:2].C(P(C(C)(C)C)C1C=CC=CC=1)(C)(C)C.[F:29][C:30]([F:43])([F:42])[C:31]1[CH:32]=[C:33](Br)[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1.C1(N(C)C)CCCCC1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.CC(N(C)C)=O>[C:1]([C:3]1[CH:4]([C:10]([F:12])([F:13])[F:11])[N:5]([C:33]2[CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=[C:31]([C:30]([F:29])([F:43])[F:42])[CH:32]=2)[N:6]([CH3:9])[C:7]=1[CH3:8])#[CH:2]

Participants

Conditions

Temperature: 110 °C

Procedure

183 mg (0.983 mmol) of 4-ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole, 2.3 mg (0.01 mmol) of palladium acetate and 3.9 mg (0.02 mmol) of copper(I) iodide are weighed into a round-bottom flask and placed under protective gas. Subsequently, 9.1 mg (0.04 mmol) of di(tertbutyl)phenylphosphine, 300 mg (1.03 mmol) of 3,5-bis(trifluoromethyl)bromobenzene, 137 mg (1.08 mmol) of cyclohexyldimethylamine and dimethylacetamide (5 ml) are added and the mixture is heated to 110° C. for 12 h. After the end of the reaction, the mixture is cooled, poured onto cold, dilute hydrochloric acid and extracted with ether. The combined ether phases which have been dried over MgSO4 are concentrated. The product is obtained as a solid in an 85% yield.

Workup

customAfter the end of the reaction
temperaturethe mixture is cooled
extractionextracted with ether
dry with materialThe combined ether phases which have been dried over MgSO4
concentrationare concentrated
customThe product is obtained as a solid in an 85% yield

Sources & evidence

ORD record: ord-2135ce7514b2449581e5a475f9133f14
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238722B2

Reaction notes

Loading…