N-(6-Chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide → N-(6-Ethyl-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878254Notes

Reaction equation

HRID 878254 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH:3]=1.[CH2:33]([Zn]CC)[CH3:34]>C1COCC1>[CH2:33]([C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:11]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=2)=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH:3]=1)[CH3:34]

Participants

4

Reactant 2

HCID 60197100N-(6-Chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamideHCID 178418750HCID 178418750, compound

Product 1

HCID 86670805N-(6-Ethyl-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(6-chloro-4-o-tolylpyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)-benzamide (0.1 g, 212 μmol, example 12) in THF (1 mL) were added tetrakis(triphenyl-phosphine)palladium(0) (12.2 mg, 10.6 μmol) and diethylzinc (1M solution in n-hexane, 137 μL, 137 μmol) and the brown solution was stirred at reflux for 16 hours. The solvent was evaporated and the brown gum was diluted with 1M aqueous HCl and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). Light yellow solid (0.051 g; 51%). MS (ESI): m/z=467.16 [M+H]+.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was evaporated
  3. additionthe brown gum was diluted with 1M aqueous HCl and EtOAc
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted twice with EtOAc
  6. washThe organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. additiontreated with silica gel
  10. customevaporated
  11. customThe compound was purified by silica gel chromatography on a 10 g column
  12. washeluting with a gradient of n-heptane:EtOAc (100:0 to 30:70)

Sources & evidence

ORD record
ord-14e6fd6ddb774ef89569f89b6b9505e0
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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