Dibutyltin oxide → HCID 22467240, compound

HRID 381313Notes

Reaction equation

HRID 381313 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.C([Sn](=O)CCCC)CCC.[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]([C:43]3[C:51]4[C:46](=[CH:47][C:48]([C:52]#[N:53])=[CH:49][CH:50]=4)[N:45]([CH3:54])[CH:44]=3)[C:28]([NH:30][S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:36][CH:35]=3)(=[O:33])=[O:32])=[O:29])=[CH:26][C:21]=2[O:20][CH2:19]1>C1(C)C=CC=CC=1>[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]([C:43]3[C:51]4[C:46](=[CH:47][C:48]([C:52]5[N:5]=[N:6][NH:7][N:53]=5)=[CH:49][CH:50]=4)[N:45]([CH3:54])[CH:44]=3)[C:28]([NH:30][S:31]([C:34]3[CH:35]=[CH:36][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:38][CH:39]=3)(=[O:32])=[O:33])=[O:29])=[CH:26][C:21]=2[O:20][CH2:19]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxide2×HCID 78378Azidotrimethylsilane2×HCID 22467231HCID 22467231, compound2×

Product 1

HCID 22467240HCID 22467240, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethylsilylazide (0.23 ml, 1.74 mmol) and dibutyl tin oxide (52 mg, 0.2 mmol) were added to a solution of 3-{1-(1,3-benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl}-6-cyano-1-methyl-1H-indole (the product of Example 51, 300 mg, 0.58 mmol) in toluene (10 ml) and the solution was heated at reflux under an atmosphere of nitrogen for 14 h. The analysis showed incomplete reaction. Further aliquots of trimethylsilylazide (0.23 ml, 1.74 mmol) and dibutyl tin oxide (52 mg, 0.2 mmol) were added and heating was continued at reflux for a further 24 h. The reaction was cooled and concentrated. The crude product was purified by flash column chromatography (gradient elution from 95% dichloromethane/5% methanol to 90% dichloromethane/10% methanol) giving a pale pink solid (100 mg).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux under an atmosphere of nitrogen for 14 h
  3. customreaction
  4. temperatureheating
  5. temperatureat reflux for a further 24 h
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (gradient elution from 95% dichloromethane/5% methanol to 90% dichloromethane/10% methanol)

Sources & evidence

ORD record
ord-f1a6cc823ea042af878423995957d918
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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