Ammonia → HCID 10361597, Verbindung

HRID 25361

Reaktionsgleichung

Reaktionsgleichung von HRID 25361
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)(=[O:20])=[O:19])=[CH:14][CH:15]=2)[C:10]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:9]1)=O)(C)(C)C.I[Si](C)(C)C.N>C(Cl)(Cl)Cl>[F:27][C:23]1[CH:22]=[C:21]([S:18]([NH:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][N:9]=[C:10]3[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 85247Trimethylsilyl iodideHCID 22567057N-(N-tert-butoxycarbonyl-3-phenyl-1H-indazol-5-yl)-3-fluorobenzenesulfonamide

Produkt 1

HCID 10361597HCID 10361597, VerbindungAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3-Fluoro-N-(3-phenyl-1H-indazol-5-yl)-benzenesulfonamide can be obtained in the following way: a solution of 0.4 g of N-(N-tert-butoxycarbonyl-3-phenyl-1H-indazol-5-yl)-3-fluorobenzenesulfonamide, of 3.5 ml of chloroform and of 0.127 ml of iodotrimethylsilane is maintained with stirring for 18 hours at a temperature in the region of 20° C. 10 ml of 5% aqueous ammonia are added to the reaction medium, which is extracted with 40 ml of dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture. The gray solid thus obtained is recrystallized from 25 ml of dichloromethane in the presence of 3 S black. 0.1 g of 3-fluoro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide is thus obtained in the form of a white solid melting at 200° C. (analysis C19H14FN3O2S % calculated C, 62.11; H, 3.84; F, 5.17; N, 11.44. % found C, 62.09; H, 3.69; F, 4.88; N, 11.44).

Aufarbeitung

  1. extractionis extracted with 40 ml of dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue thus obtained
  6. customis purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture
  7. customThe gray solid thus obtained
  8. customis recrystallized from 25 ml of dichloromethane in the presence of 3 S black

Quellen und Nachweise

ORD-Eintrag
ord-9030238253fd4a1187754a4b2f328d9d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858638B2

Verknüpfte Notizen

Wird geladen…