Ammonia → HCID 10361597, compound

HRID 25361

Reaction equation

HRID 25361 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 10361597HCID 10361597, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9030238253fd4a1187754a4b2f328d9d
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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