Triethylamine → HCID 15748266, compound

HRID 1029472Notes

Reaction equation

HRID 1029472 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.Br[C:16]1[C:17]([CH:38]([CH3:40])[CH3:39])=[N:18][N:19]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1>CN(C=O)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[N:19]([C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)[N:18]=[C:17]([CH:38]([CH3:40])[CH3:39])[C:16]=2/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 15748263HCID 15748263, compound

Product 1

HCID 15748266HCID 15748266, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl acrylate (4.9 mL, 45 mmoles) and bis-triphenyl phosphine palladium (II) chloride (0.25 g, 0.36 mmoles) were suspended in a 1:1 mixture of triethyl amine and DMF. This mixture was heated to reflux under an atmosphere of N2. When the suspension had completely dissolved, 2-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]quinoline (3.70 g, 9.0 mmoles) was carefully added. The resulting yellow solution was refluxed for 16 hours, then cooled and partitioned between H2O and Et2O. The ether layer was dried over MgSO4, filtered, and evaporated to give a yellow solid which was recrystallized from hexanes to give 3.36 g (87%) of the title compound as a tan solid, mp 140°-143° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux under an atmosphere of N2
  3. dissolutionWhen the suspension had completely dissolved
  4. temperatureThe resulting yellow solution was refluxed for 16 hours
  5. temperaturecooled
  6. custompartitioned between H2O and Et2O
  7. dry with materialThe ether layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give a yellow solid which
  11. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-6d86b7f7348d48cea1877f9bbff23405
Source dataset
uspto-grants-1992_04
Patent number
US05102893

Reaction notes

Loading…