5-Bromo-3-methylisoquinoline → 5-Allyl-3-methylisoquinoline

HRID 585969Notes

Reaction equation

HRID 585969 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9](Br)[CH:8]=[CH:7][CH:6]=2.[CH2:13]([CH:17]([Sn])C=C(CCCC)CCCC)[CH2:14]CC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:17]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]2)[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 218161685-Bromo-3-methylisoquinolineHCID 86589045Tributylallyltin

Product 1

HCID 223376835-Allyl-3-methylisoquinoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-5-bromoisoquinoline (1.0 g, 4.5 mmol), tributylallyltin (1.6 mL, 5.0 mmol), and dichlrobis(tri-o-tolylphosphine)palladium (II) were combined in toluene (100 mL) and refluxed for 14 hours. The mixture was cooled, diluted with ethyl acetate, and washed twice with aqueous NH4Cl. The organic phase was separated, concentrated, and the residue was purified by chromatography (ethyl acetate:hexanes, 30:70) to provide the title compound. 1H NMR (300 MHz, d6-DMSO) 9.21 (s, 1H), 8.00 (d, 1H), 7.63 (m, 2H), 7.58 (m, 1H), 4.18 (s, 2H), 3.62 (s, 3H), 2.62 (s, 3H). MS (DCI/NH3) m/e 216 (M+H)+.

Workup

  1. temperaturerefluxed for 14 hours
  2. temperatureThe mixture was cooled
  3. washwashed twice with aqueous NH4Cl
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography (ethyl acetate:hexanes, 30:70)

Sources & evidence

ORD record
ord-f5d6ca98a5374e2495744cfd08950dbf
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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