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

HRID 469772

Reaction equation

HRID 469772 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=2)[C:7]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:6][CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:7]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])=[N:6][CH:5]=1

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 57.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester (Example 2a, 163 mg, 517 μmmol) was dissolved in ethanol (5 mL). Palladium (10% on charcoal, 16.3 mg, 517 mmol) was added; the suspension was evacuated, flushed with hydrogen gas 3 times and stirred for 1.5 h at ambient temperature. The reaction mixture was filtered through Celite® and concentrated in vacuo to give the title compound (95 mg, quant.) as grey solid that was used in the subsequent reactions without further purification; MS (ESI) 318.1 (M+H)+.

Workup

  1. customthe suspension was evacuated
  2. customflushed with hydrogen gas 3 times
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43ee755bbd6644c4ad372a307485cea6
Source dataset
uspto-grants-2014_01
Patent number
US08629166B2

Linked notes

Loading…