Dibutyltin oxide → HCID 178449254, compound

HRID 396200Notes

Reaction equation

HRID 396200 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[N:9]([CH2:27][CH2:28][CH2:29][C:30]#[N:31])[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])=[CH:12][CH:11]=2)=[O:7])[CH:2]([CH3:4])[CH3:3].[N:32]([Si](C)(C)C)=[N+:33]=[N-:34].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([NH:5][C:6]([C:8]1[N:9]([CH2:27][CH2:28][CH2:29][C:30]2[NH:34][N:33]=[N:32][N:31]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])=[CH:12][CH:11]=2)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 70029876HCID 70029876, compound

Product 1

HCID 178449254HCID 178449254, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(3-cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid isobutyl amide (0.076 g, 0.17 mmol) in toluene (10 mL) was added azidotrimethylsilane (0.066 mL, 0.50 mmol) and dibutyltin oxide (0.012 g, 0.050 mmol). The reaction mixture was heated to reflux and stirred under argon at reflux temperature for 40 h. The solution was then cooled and the toluene removed under reduced pressure. Methanol was 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 (0.032 g, 38%). MS(ES) m/e 501.2 [M +H]+.

Workup

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

Sources & evidence

ORD record
ord-6a602fb3cdd44328bd66b05b3c4d1bb0
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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