5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester → Methyl 5-cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinate

HRID 240697Notes

Reaction equation

HRID 240697 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[C:9]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[CH:10]=1)=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 712944455-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester

Product 1

HCID 71294015Methyl 5-cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinateYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid methyl ester (163 mg, 517 μmol) was combined with ethanol (5 mL) to give a colorless solution. Palladium (10% on charcoal, 16.3 mg, 517 μmol) was added and the suspension was evacuated and flushed with hydrogen 3 times and stirred for 1.5 h at ambient temperature. Afterwards the reaction mixture was filtered through Celite and concentrated in vacuo to give the title compound (95 mg, 58%) as grey solid; MS (EI) 318.1 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customthe suspension was evacuated
  3. customflushed with hydrogen 3 times
  4. filtrationAfterwards the reaction mixture was filtered through Celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b4d92921d5549a797b84cf4dbe6f7e0
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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