Dibutyltin oxide → HCID 178458778, compound

HRID 396207Notes

Reaction equation

HRID 396207 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])[CH:10]=[C:9]2[C:20](=[O:23])[CH2:21][CH3:22].[N:29]([Si](C)(C)C)=[N+:30]=[N-:31].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[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]1[NH:31][N:30]=[N:29][N:19]=1)[CH:10]=[C:9]2[C:20](=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 23003162HCID 23003162, compound

Product 1

HCID 178458778HCID 178458778, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[5-(2,6-dichlorobenzyloxy)-3-propionyl-indol-1-yl]butyronitrile (0.034 g, 0.08 mmol) in toluene (3 mL) was added azidotrimethylsilane (0.033 mL, 0.25 mmol) and dibutyltin oxide (0.006 g, 0.02 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 white solid (0.017 g, 46%). MS(ES) m/e 458.0 [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-a2b90da1030f4fe18ebccdaa3f35fee5
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

Loading…