Tributylstannane → 2-Methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde

HRID 2303958Notes

Reaction equation

HRID 2303958 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15]I)[CH:7]=[C:6]2[CH:17]=[O:18].N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.C([SnH](CCCC)CCCC)CCC.[F-].[K+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][CH2:14][CH2:15][C:7]1=[C:6]2[CH:17]=[O:18]

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 522689Potassium FluorideHCID 184620695-Methoxy-1-(4-iodobutyl)indole-3-carboxaldehyde

Product 1

HCID 184620802-Methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 5-methoxy-1-(4-iodobutyl)indole-3-carboxaldehyde in toluene at reflux under argon is added dropwise over 2 h a solution of 1,1′-azobis(cyclohexanecarbonitrile) and tri-n-butyltin hydride in toluene. The mixture is stirred for 3 h, cooled to room temperature, and potassium fluoride and water are added. The mixture is stirred for 18 h and filtered through a pad of kieselguhr. The filter-cake is washed (ethyl acetate) and the filtrate is concentrated in vacuo and purified by column chromatography to give the product.

Workup

  1. stirringThe mixture is stirred for 18 h
  2. filtrationfiltered through a pad of kieselguhr
  3. washThe filter-cake is washed (ethyl acetate)
  4. concentrationthe filtrate is concentrated in vacuo
  5. custompurified by column chromatography
  6. customto give the product

Sources & evidence

ORD record
ord-9dc1da1498bb46ec81e98f920a17a814
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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