Dibutyltin oxide → HCID 178427404, compound

HRID 520510Notes

Reaction equation

HRID 520510 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3[S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[C:15]([C:32]#[N:33])[CH:14]=2)=[CH:4][N:3]=1.C[Si]([N:38]=[N+:39]=[N-:40])(C)C.C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3[S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[C:15]([C:32]3[NH:40][N:39]=[N:38][N:33]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 87111387HCID 87111387, compound

Product 1

HCID 178427404HCID 178427404, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

N-(2-Chloro-5-{4-cyano-1-[(4-methylphenyl)sulfonyl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (1.6 g, 3.19 mmol), trimethylsilyl azide (0.734 g, 6.37 mmol) and dibutyl(oxo)stannane (0.079 g, 0.319 mmol) were placed in toluene (30 ml) and the mixture heated at 100° C. for 16 h. The mixture was stirred at this temperature over the weekend. The mixture was cooled to room temperature and the solvent removed in vacuo. The residue was adsorbed onto florisil and chromatographed on silica (100 g cartridge) eluting with 0-100% ethyl acetate in cyclohexane followed by 0-20% methanol to give the title compound (1.3 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed in vacuo
  3. customchromatographed on silica (100 g cartridge)
  4. washeluting with 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-6f8f891f7d154e9c89495405e8bff5a5
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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