N,N'-Dimethylethylenediamine → HCID 67169502, compound

HRID 872535Notes

Reaction equation

HRID 872535 reaction equation
Br/[CH:2]=[CH:3]/[C:4]1[O:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([NH2:34])=[O:33].CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[O:5][C:4](/[CH:3]=[CH:2]/[NH:34][C:32](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)=[CH:8][CH:7]=2)=[CH:10][C:11]=1[C:16]([F:19])([F:18])[F:17]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 150702-PyridinecarboxamideHCID 86670239HCID 86670239, compound

Product 1

HCID 67169502HCID 67169502, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

(E)-2-(2-bromovinyl)-5-(4-chloro-3-(trifluoromethyl)phenyl)furan (0.501 g, 1.378 mmol) in toluene (2.4 ml) was added to a mixture of copper(I) iodide (0.014 g, 0.069 mmol), potassium carbonate (0.381 g, 2.756 mmol), picolinamide (0.202 g, 1.654 mmol) and N,N′-dimethylethylene diamine (0.0149 ml, 0.0138 mmol) under nitrogen. The reaction mixture was refluxed for 7.5 h and allowed to cool to RT. It was then filtrated through a layer of silica and the filter cake was washed with EtOAc. The filtrate was evaporated to dryness and purified with CombiFlash using heptane-DCM as eluent system affording 0.046 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 6.54 (d, 1H), 6.70 (d, 1H), 7.26 (d, 1H), 7.61-7.70 (m, 2H), 7.77 (d, 1H), 7.99-8.02 (m, 1H), 8.04-8.09 (m, 2H), 8.13 (m, 1H), 8.74 (m, 1H), 11.20 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 7.5 h
  2. filtrationIt was then filtrated through a layer of silica
  3. washthe filter cake was washed with EtOAc
  4. customThe filtrate was evaporated to dryness
  5. custompurified with CombiFlash

Sources & evidence

ORD record
ord-842febdff82440969fc89bc0b126aca6
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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