5-Cyclohex-1-enyl-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide → 5-cyclohexyl-N-pyridin-3-yl-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

HRID 469777Notes

Reaction equation

HRID 469777 reaction equation
[C:1]1([C:7]2[C:8]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:9][CH:10]=[C:11]([CH:21]=2)[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:7]2[C:8]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[N:9][CH:10]=[C:11]([CH:21]=2)[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 712943555-Cyclohex-1-enyl-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide

Product 1

HCID 712944495-cyclohexyl-N-pyridin-3-yl-6-(2,2,2-trifluoro-ethoxy)-nicotinamideYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Cyclohex-1-enyl-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide (Example 1c, 0.012 g, 31.8 μmol) was dissolved in ethyl acetate (1 mL). Palladium (10% on charcoal, 3.4 mg, 32 μmol) was added; the suspension was degassed and aerated with argon (5×). Then it was degassed and aerated with hydrogen (3×) and stirred for 20 h under hydrogen. The reaction mixture was degassed and aerated with argon (3×) again. Then it was filtered through dicalite, washed with i-propyl acetate and concentrated in vacuo to give the title compound (11 mg, 91%) as white solid; MS (ESI) 380.3 (M+H)+.

Workup

  1. customthe suspension was degassed
  2. customThen it was degassed
  3. customThe reaction mixture was degassed
  4. filtrationThen it was filtered through dicalite
  5. washwashed with i-propyl acetate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b6c61d1b59c4bf0a0fa00d307790ff4
Source dataset
uspto-grants-2014_01
Patent number
US08629166B2

Reaction notes

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