Dibutyltin oxide → HCID 178502632, compound

HRID 396210Notes

Reaction equation

HRID 396210 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[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])[C:10]([CH:20]=[N:21][O:22][CH3:23])=[CH:9]2.[N:29]([Si](C)(C)C)=[N+:30]=[N-:31].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:23][O:22][N:21]=[CH:20][C:10]1[N:11]([CH2:15][CH2:16][CH2:17][C:18]2[NH:31][N:30]=[N:29][N:19]=2)[C:12]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:5][CH2:4][C:3]1[C:24]([Cl:28])=[CH:25][CH:26]=[CH:27][C:2]=1[Cl:1])=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 86759105HCID 86759105, compound

Product 1

HCID 178502632HCID 178502632, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[5-(2,6-dichlorobenzyloxy)-2-(methoxyiminomethyl)indol-1-yl]butyronitrile (0.07 g, 0.17 mmol) in toluene (3 mL) was added azidotrimethylsilane (0.067 mL, 0.55 mmol) and dibutyltin oxide (0.014 g, 0.055 mmol). The reaction was refluxed for 16 h. The solvent was removed under reduced pressure and the crude product was purified by HPLC to yield a yellow foaming solid (0.045 g, 58%). MS(ES) m/e 459.0 [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 HPLC

Sources & evidence

ORD record
ord-3e659dca08ce4eabb4e61d426b71d8e6
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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