2-(Tributylstannyl)furan → 6-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dione

HRID 2236470Notes

Reaction equation

HRID 2236470 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][O:15][CH3:16].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[Sn](CCCC)(CCCC)CCCC>CN(C)C=O.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>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][O:15][CH3:16]

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 686963676-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dioneYield 68%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (1.24 g, 4.4 mmol) and PdCl2(PPh3)2 (200 mg, 0.28 mmol) and 2-furyltributyltin (2 g, 5.6 mmol) in N,N-dimethylformamide (20 mL) is degassed and heated at 100° C. for 1 hour. Upon cooling to room temperature, the product precipitated out. After filtration, the precipitate is washed with Et2O and dried to provide the desired product (800 mg, 68%). MS (ESI): 270.1 (M+1)+1.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe product precipitated out
  3. filtrationAfter filtration
  4. washthe precipitate is washed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-588e3cbfbf4a4d1cb978aac0414568c0
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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