Stannane, tributyl(1-ethoxyethenyl)- → 6-acetyl-3,4-dihydro-2H-isoquinolin-1-one

HRID 2245706Notes

Reaction equation

HRID 2245706 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[C:18]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2)(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 592164656-acetyl-3,4-dihydro-2H-isoquinolin-1-oneYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a flask charged with 1.55 g of (PPh3)2PdCl2 and 5.0 g of 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one was added 25 mL of DMF. Then 9.58 g of Tributyl-(1-ethoxy-vinyl)-stannane was added and the reaction mixture was heated to 110° C. and stirred until completion of the reaction. The reaction mixture was filtered over celite and diluted with diethyl ether. After washing with saturated ammonium carbonate, water and brine, the solution was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting mixture dissolved in THF and treated with 3.0 M aqueous HCl to effect hydrolysis. The mixture was then partitioned between water and diethyl ether. The organic phase was washed sequentially with saturated sodium bicarbonate, water, and brine and then dried over sodium sulfate. After filtration, the solution was concentrated and purified by flash chromatography to afford the 3.28 g of 6-Acetyl-3,4-dihydro-2H-isoquinolin-1-one.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. additiondiluted with diethyl ether
  3. washAfter washing with saturated ammonium carbonate, water and brine
  4. dry with materialthe solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting mixture dissolved in THF
  8. additiontreated with 3.0 M aqueous HCl
  9. customhydrolysis
  10. customThe mixture was then partitioned between water and diethyl ether
  11. washThe organic phase was washed sequentially with saturated sodium bicarbonate, water, and brine
  12. dry with materialdried over sodium sulfate
  13. filtrationAfter filtration
  14. concentrationthe solution was concentrated
  15. custompurified by flash chromatography

Sources & evidence

ORD record
ord-621d0fd0c886400cb1a43bff16fc0116
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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