Dibutyltin oxide → HCID 178478103, compound

HRID 396204Notes

Reaction equation

HRID 396204 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH:10]=[CH:9]2.[N:25]([Si](C)(C)C)=[N+:26]=[N-:27].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]1[NH:27][N:26]=[N:25][N:19]=1)[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 23003165HCID 23003165, compound

Product 1

HCID 178478103HCID 178478103, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[5-(2,6-dichlorobenzyloxy)indole-1-yl]butyronitrile (0.1 g, 0.28 mmol) in toluene (3 mL) was added azidotrimethylsilane (0.11 mL, 0.83 mmol) and dibutyltin oxide (0.021 g, 0.083 mmol). The reaction was refluxed for 16 h. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (silica gel, dichloromethane/methanol) to yield a white foaming solid (0.067 g, 59%). MS(ES) m/e 402.0 [M+H]+.

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by flash column chromatography (silica gel, dichloromethane/methanol)

Sources & evidence

ORD record
ord-11f3b3914c6a42b0a4785c90e2577022
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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