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

HRID 1767553Notes

Reaction equation

HRID 1767553 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. additionare added to the reaction mixture, which
  3. temperatureis maintained
  4. temperatureat reflux for 24 hours
  5. customAfter returning to room temperature
  6. customevaporation to dryness
  7. extractionhydrolysed and subsequently extracted with ethyl acetate
  8. dry with materialThe organic phase is dried over magnesium sulphate
  9. concentrationconcentrated
  10. custompurified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-0e056545b03b4283bb4e843ec8d9c06a
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

Loading…