Tributylstannane → 2-Methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizine-10-carbaldehyde

HRID 2298763Notes

Reaction equation

HRID 2298763 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([CH:17]=[O:18])=[CH:7]1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][C:14]2[N:6]3[C:7]([CH2:2][CH2:3][CH2:4][CH2:5]3)=[C:8]([CH:17]=[O:18])[C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 112898921-(4-Bromobutyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

Product 1

HCID 112532192-Methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizine-10-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under argon, a solution containing 2.70 g (8.67 mmol) of the compound obtained in Step B and 1.45 g (8.67 mmol) of AIBN in 80 ml of toluene is brought to reflux. After stirring for 20 minutes, 4.67 ml (17.35 mmol) of tributyltin hydride in 100 ml of toluene are added to the reaction mixture, which is maintained at reflux for 24 hours. After returning to room temperature and evaporation to dryness, the residue is then hydrolysed and subsequently extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel. (eluant: petroleum ether/ethyl acetate, 95:5) to yield the title product in the form of a yellow oil.

Workup

  1. temperatureto reflux
  2. temperatureis maintained
  3. temperatureat reflux for 24 hours
  4. customAfter returning to room temperature
  5. customevaporation to dryness
  6. extractionhydrolysed and subsequently extracted with ethyl acetate
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. concentrationconcentrated
  9. custompurified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-89585bc5b24b4a66beb0b35fa9f95aaa
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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