HCID 68552252, compound → HCID 57418374, compound

HRID 1868153Notes

Reaction equation

HRID 1868153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)(=[O:16])=[O:15])[CH:10]([CH3:26])[CH2:9]2)=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=3)[NH2:23])(=[O:16])=[O:15])[C@H:10]([CH3:26])[CH2:9]2)=[C:4]([C:27]([F:28])([F:29])[F:30])[CH:3]=1

Participants

4

Reactant 1

HCID 68552252HCID 68552252, compound

Product 1

HCID 57418374HCID 57418374, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-Fluoro-2-trifluoromethyl-phenyl)-2-methyl-1-(3-nitro-benzenesulfonyl)-piperazine (330 mg, 0.8 mmol) and a catalytic amount of 10% Pd/C in EtOAc (25 mL) was stirred under H2 (1 atm) at ambient temperature for two hours, after which the reduction was judged complete by TLC. The H2 removed under vacuum, and the reaction mixture was filtered through celite, and rinsed with EtOAc (3×25 mL), and the filtrate was concentrated in vacuo, affording 180 mg of the desired sulfonamide in >95% purity (62% yield). HRMS: calcd for C18H19F4N3O2S+H+, 418.12068. found ([M+H]+), 418.12119.

Workup

  1. customThe H2 removed under vacuum
  2. filtrationthe reaction mixture was filtered through celite
  3. washrinsed with EtOAc (3×25 mL)
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d69aedf4b3bc4a95a064e3ee98e5bf28
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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