Ethylene → 4-Ethenylisoquinoline

HRID 496406Notes

Reaction equation

HRID 496406 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[CH3:12][CH2:13]N(CC)CC.C=C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1)=[CH2:13]

Participants

6

Reactant 3

HCID 6325EthyleneHCID 8471TriethylamineHCID 737434-Bromoisoquinoline

Product 1

HCID 223247694-EthenylisoquinolineYield 94%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromoisoquinoline (10 g, 0.048 mol), Pd(OAc)2 (1.07 g, 0.0048 mol), (o-tol)3P (2.95 g, 0.0096 mol), Et3N (13.06 mL, 0.096 mol) and a saturated soln. of ethylene in MeCN (100 mL) were placed in a seal reaction apparatus and heated to 100° C. for 2 days. Solvent was removed in vacuo and EtOAc was added. Washed the organic layer with H2O (2×), sat. NaHCO3 (2×), and brine. The organic solution was dried over MgSO4 and the solvent was removed in vacuo. A brown oil (7.0 g) was obtained and chromatographed using SiO2, DCM/1% MeOH to DCM/2%MeOH giving a yellow oil (5.57 g, 75% yield). MS APCI (156), [M+H]+; anal. calcd. for C11H9N1.0.07H2O, MWC=156.46, C, 84.44%; H, 5.89%; N, 8.95%. found C, 84.48%; H, 5.84%; N, 8.66%.

Workup

  1. customSolvent was removed in vacuo and EtOAc
  2. additionwas added
  3. washWashed the organic layer with H2O (2×), sat. NaHCO3 (2×), and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5e2d9284d9a34f5d92ffcdca64b592a5
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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