Dibutyltin oxide → HCID 178464175, compound

HRID 396201Notes

Reaction equation

HRID 396201 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[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:32]([Si](C)(C)C)=[N+:33]=[N-:34].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[N:7]([CH2:25][CH2:26][CH2:27][C:28]2[NH:34][N:33]=[N:32][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])[CH3:31]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 70029571HCID 70029571, compound

Product 1

HCID 178464175HCID 178464175, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(3-cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid diethylamide (0.078 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 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 (0.040 g, 47%). 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 cooled
  5. customthe toluene removed under reduced pressure
  6. additionMethanol was then 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-2eb933bdeae3412981f7676b2826d460
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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