Dibutyltin oxide → HCID 178427403, compound

HRID 520531Notes

Reaction equation

HRID 520531 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([C:28]#[N:29])[C:13]4[CH:14]=[N:15][N:16]([S:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:30]1[C:38]2[C:33](=[C:34]([C:39]3[CH:40]=[C:41]([C:58]#[N:59])[C:42]4[CH:43]=[N:44][N:45]([S:48]([C:51]5[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=5)(=[O:50])=[O:49])[C:46]=4[CH:47]=3)[CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1.C[Si]([N:64]=[N+:65]=[N-:66])(C)C.C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1>[NH:30]1[C:38]2[C:33](=[C:34]([C:39]3[CH:47]=[C:46]4[C:42]([CH:43]=[N:44][N:45]4[S:48]([C:51]4[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=4)(=[O:50])=[O:49])=[C:41]([C:58]4[NH:66][N:65]=[N:64][N:59]=4)[CH:40]=3)[CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1.[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[C:12]([C:28]4[NH:66][N:65]=[N:64][N:29]=4)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2×HCID 666940066-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrileHCID 667767806-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile

Product 1

HCID 178427403HCID 178427403, compoundYield 141.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

6-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile (0.669 g, 1.679 mmol) and 6-(1H-indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile (0.561 g, 1.360 mmol) were slurried in toluene (60 ml) and treated with trimethylsilyl azide (0.887 ml, 6.68 mmol) and dibutyl(oxo)stannane (0.151 g, 0.608 mmol). The reaction mixture was heated, under nitrogen at 120° C. for 16 h, then additional trimethylsilyl azide (0.221 ml, 1.67 mmol) was added. After heating for a further 2 h, the solution was evaporated to dryness, treated with methanol (30 ml) and absorbed onto Florisil. The Florisil was loaded onto a silica cartridge (100 g) which was eluted with 0-30% methanol+1% triethylamine/dichloromethane. The appropriate fractions were combined and concentrated to give the title compound as a brown solid (1.724 g).

Workup

  1. temperatureAfter heating for a further 2 h
  2. customthe solution was evaporated to dryness
  3. additiontreated with methanol (30 ml)
  4. customabsorbed onto Florisil
  5. washwas eluted with 0-30% methanol+1% triethylamine/dichloromethane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab45176c354a4cb48c592a6f228eb966
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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