Tributylstannane → 7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxaldehyde

HRID 2303950Notes

Reaction equation

HRID 2303950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13]I)[CH:6]=[C:5]2[CH:15]=[O:16].N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.C([SnH](CCCC)CCCC)CCC.[F-].[K+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[C:5]([CH:15]=[O:16])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 522689Potassium FluorideHCID 184621165-Chloro-1-(3-iodopropyl)indole-3-carboxaldehyde

Product 1

HCID 184620977-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxaldehydeYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 5-chloro-1-(3-iodopropyl)indole-3-carboxaldehyde (5.0 g, 14 mmol) in toluene (75 mL) at reflux under argon was added dropwise over 2 h a solution of 1,1′-azobis(cyclohexanecarbonitrile) (3.5 g, 14 mmol) and tri-n-butyltin hydride (7.8 mL, 29 mmol) in toluene (75 mL). The mixture was stirred for 3 h, cooled to room temperature, and potassiurn fluoride (3.5 g, 60 mmol) and water (15 mL) were added. The mixture was stirred for 18 h and filtered through a pad of kieselguhr. The filter-cake was washed (ethyl acetate) and the filtrate was concentrated in vacuo, purified by colurnn chromatography [SiO2; ethyl acetate-hexane (9:1)] and recrystallised (methanol) to give the product as a white solid (1.1 g, 36%): mp 179-180° C.; Found: C, 65.54; H, 4.61; N, 6.38%. C12H10ClNO requires: C, 65.61; H, 4.59; N, 6.37%.

Workup

  1. stirringThe mixture was stirred for 18 h
  2. filtrationfiltered through a pad of kieselguhr
  3. washThe filter-cake was washed (ethyl acetate)
  4. concentrationthe filtrate was concentrated in vacuo
  5. custompurified by colurnn chromatography [SiO2; ethyl acetate-hexane (9:1)]
  6. customrecrystallised (methanol)

Sources & evidence

ORD record
ord-69fd01538f54495399394a7ba5829b60
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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