Chlorotrimethylsilane → HCID 21995562, compound

HRID 989212Notes

Reaction equation

HRID 989212 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH:2]=1.Cl[Si](C)(C)C.[C:23](C1NC=CN=1)(C1NC=CN=1)=[O:24].[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][C:45]=1[C:46]([F:49])([F:48])[F:47])[NH:42][CH2:41][CH2:40]2>C(Cl)(Cl)Cl.O.CN(C)C=O.C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([NH:17][C:23]([N:42]3[C:43]4[C:39](=[CH:38][C:37]([O:36][CH3:35])=[C:45]([C:46]([F:49])([F:47])[F:48])[CH:44]=4)[CH2:40][CH2:41]3)=[O:24])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH:2]=1

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 16792745HCID 16792745, compound

Product 1

HCID 21995562HCID 21995562, compoundYield 60.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(pyrid-3-ylaminosulphonyl)-aminobenzene (D39) (0.5 g, 2 mmol) in chloroform (40 ml) was treated with triethylamine (5 ml) and chlorotrimethylsilane (5 ml). The solution was evaporated to dryness, and the residue dissolved in dichloromethane (20 ml). Carbonyl diimidazole (0.32 g, 2 mmol) was added and after 1 h the reaction mixture was evaporated to dryness. Dimethylformamide (20 ml) and (5-methoxy-6-trifluoromethyl indoline (0.43 g, 2 mmol) was added, and the mixture heated to 100° C. for 2 h. The cooled solution was diluted with water (60 ml). Filtration and drying afforded a brown solid (0.6 g). Chromatography, eluting with 0-5% methanol in ethyl acetate afforded the product as a white solid (0.26 g, 26%), m.p.>215° C.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in dichloromethane (20 ml)
  3. customwas evaporated to dryness
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-fe0a7caa5f04410fb8b336afec7fa8c5
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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