N-{3-[(E)-2-(4-fluorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide → HCID 178504716, compound

HRID 25429Notes

Reaction equation

HRID 25429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=3)[NH:12][N:11]=2)=[CH:4][CH:3]=1.[H][H]>[Pd].CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=3)[NH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 22567051N-{3-[(E)-2-(4-fluorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 178504716HCID 178504716, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

N-{3-[2-(4-Fluorophenyl)ethyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: a mixture of 300 mg of N-{3-[(E)-2-(4-fluorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide, of 30 mg of 10% palladium-on-charcoal and of 8 ml of dimethylformamide is autoclaved under a pressure of 10 bar of hydrogen and the mixture is stirred at a temperature in the region of 20° C. for 1 hour until complete absorption of hydrogen. The medium is then filtered through a bed of Celite® 535, this is washed with dimethylformamide and the filtrate is concentrated to dryness under reduced pressure. The solid residue is taken up with dichloromethane and the insoluble material is isolated by filtration, washed with dichloromethane and then dried under reduced pressure. 220 mg of N-{3-[2-(4-fluorophenyl)ethyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide is thus obtained in the form of an off-white solid melting at 234° C. (analysis C22H20FN3O4S2 % calculated C, 55.81; H, 4.26; F, 4.01; N, 8.87; O, 13.51; S, 13.54. % found C, 55.80; H, 4.45; F, 3.85; N, 8.97; S, 12.80).

Workup

  1. filtrationThe medium is then filtered through a bed of Celite® 535
  2. washthis is washed with dimethylformamide
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure
  4. customthe insoluble material is isolated by filtration
  5. washwashed with dichloromethane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-38774878c3d84c63be88862e74c9b975
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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