Triethylamine → 4-Chloro-2-trifluoromethyl-8-vinyl-quinoline

HRID 505855Notes

Reaction equation

HRID 505855 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[C:7]2[Cl:16].[CH2:17](N(CC)CC)[CH3:18]>C(O)C>[Cl:16][C:7]1[C:6]2[C:11](=[C:2]([CH:17]=[CH2:18])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 6283708-Bromo-4-chloro-2-(trifluoromethyl)quinoline

Product 1

HCID 670395294-Chloro-2-trifluoromethyl-8-vinyl-quinolineYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2.00 g (6.25 mmol) 8-bromo-4-chloro-2-trifluoromethylquinoline (commercially available from Maybridge, Cornwall, UK), 258 mg (0.31 mmol) PdCl2dppf CH2Cl2, 1.29 g (9.37 mmol) potassium vinyl tetrafluoroborate and 0.88 ml (6.28 mmol) triethylamine in 40 ml ethanol was heated at reflux for 3 h. The resulting yellow suspension was filtered and the filtrate evaporated to dryness. The residue was suspended in ethyl acetate, filtered and the filtrate extracted with water. The organic layer was evaporated to dryness and the isolated crude product purified by silica gel chromatography (hexane) to yield 1.17 g (72%) of the title compound as white crystals. MS: 257.1 (M+). 1H-NMR (300 MHz, CDCl3): 5.58 (dd, J=11.1, 1.1 Hz, 1H); 6.07 (dd, J=17.8, 1.1 Hz, 1H); 7.75 (t, J=7.7 Hz, 1H); 7.81 (s, 1H); 7.99 (dd, J=17.8, 1.1 Hz, 1H); 8.09 (d, J=7.2 Hz, 1H); 8.23 (d, J=8.4 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe resulting yellow suspension was filtered
  4. customthe filtrate evaporated to dryness
  5. filtrationfiltered
  6. extractionthe filtrate extracted with water
  7. customThe organic layer was evaporated to dryness
  8. customthe isolated crude product
  9. custompurified by silica gel chromatography (hexane)

Sources & evidence

ORD record
ord-86e36a0f4eef4d159998f27b60910f0b
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

Loading…