Dibutyltin oxide → HCID 22467240, compound

HRID 1934603Notes

Reaction equation

HRID 1934603 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. Tlc 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-b3f3d2d65b7e4c6d9b394be96c77479b
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

Loading…