Dibutyltin oxide → HCID 178478102, compound

HRID 396212Notes

Reaction equation

HRID 396212 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[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]([C:20]1[O:24][CH:23]=[N:22][CH:21]=1)=[CH:9]2.[N:30]([Si](C)(C)C)=[N+:31]=[N-:32].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:2]([Cl:1])[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:32][N:31]=[N:30][N:19]=1)[C:10]([C:20]1[O:24][CH:23]=[N:22][CH:21]=1)=[CH:9]2

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 23003166HCID 23003166, compound

Product 1

HCID 178478102HCID 178478102, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[5-(2,6-dichlorobenzyloxy)-2-(oxazol-5-yl)indol-1-yl]butyronitrile (0.21 g, 0.49 mmol) in toluene (10 mL) was added azidotrimethylsilane (0.20 mL, 1.48 mmol) and dibutyltin oxide (0.037 g, 0.148 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, MeOH/CH2Cl2) to yield a yellow solid (0.18 g, 78%). MS(ES) m/e 469.0 [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, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c8298aaf64f64b848632604537872ff4
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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