Dibutyltin oxide → HCID 178468529, compound

HRID 396195Notes

Reaction equation

HRID 396195 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[N:30]([Si](C)(C)C)=[N+:31]=[N-:32].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:26][CH2:27][C:28]2[NH:32][N:31]=[N:30][N:29]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=1[Cl:23])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 70030611HCID 70030611, compound

Product 1

HCID 178468529HCID 178468529, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(3-cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid ethyl ester (0.60 g, 1.39 mmol) in toluene (30 mL) was added azidotrimethylsilane (0.55 mL, 4.17 mmol) and dibutyltin oxide (0.10 g, 0.42 mmol). The reaction mixture was heated and stirred under argon at reflux temperature for 40 h. The solution was cooled and the toluene removed under reduced pressure. Methanol was then added and removed under reduced pressure. Ethyl acetate was added and the reaction mixture was washed with water and brine. The organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by flash chromatography (silica gel, 10% methanol/dichloromethane) yielded a white solid (0.58 g, 87%). MS(ES) m/e 474.2 [M +H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 40 h
  3. temperatureThe solution was cooled
  4. customthe toluene removed under reduced pressure
  5. additionMethanol was then added
  6. customremoved under reduced pressure
  7. additionEthyl acetate was added
  8. washthe reaction mixture was washed with water and brine
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure
  12. customPurification by flash chromatography (silica gel, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-bb612fdac232474e83ec6e2e34f05e30
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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