Toluene → HCID 66661552, compound

HRID 2275605Notes

Reaction equation

HRID 2275605 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:13][C:14]([F:21])([F:20])[C:15]1[CH:19]=[CH:18][NH:17][N:16]=1.C1(C)C=CC=CC=1.CN(C)C=O.CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.[Cu]I>[F:13][C:14]([F:21])([F:20])[C:15]1[CH:19]=[CH:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]#[N:12])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[N:16]=1

Participants

9

Reactant 6

HCID 1140TolueneHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 27952731-(4-Bromophenyl)CyclopropanecarbonitrileHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 66661552HCID 66661552, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromophenyl)cyclopropanecarbonitrile (600 mg, 0.003 mol), 3-(trifluoromethyl)-1H-pyrazole (441 mg, 0.00324 mol) in toluene (2 mL, 0.02 mol) and N,N-dimethylformamide (3 mL, 0.04 mol) were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (77 mg, 0.00054 mol), copper(I) iodide (51 mg, 0.00027 mol), and potassium carbonate (784 mg, 0.00567 mol). The mixture was microwave irradiated at 200° C. for 60 minutes and then filtered. The filtrate was diluted with methanol, and the product from the filtrate was isolated and purified using prep-HPLC. Additional product could be obtained from the precipitate by dissolving the precipitate in EtOAc, washing with satd. NaHCO3, brine, drying with MgSO4, and concentrating for purification.

Workup

  1. customThe mixture was microwave irradiated at 200° C. for 60 minutes
  2. filtrationfiltered
  3. additionThe filtrate was diluted with methanol
  4. customthe product from the filtrate was isolated
  5. custompurified
  6. customAdditional product could be obtained from the precipitate
  7. washwashing with satd
  8. dry with materialNaHCO3, brine, drying with MgSO4
  9. concentrationconcentrating for purification

Sources & evidence

ORD record
ord-efe171f6eccb49f9a71f5fb601cb0171
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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