2,4,6-Trifluorobenzenesulfonyl chloride → 2,4,6-Trifluoro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

HRID 1868412

Reaction equation

HRID 1868412 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:19]=1[S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1.Cl>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:19]=1[S:26]([NH:14][CH:3]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[C:2]([F:1])([F:15])[F:16])(=[O:28])=[O:27]

Participants

5

Reactant 2

HCID 27769832,4,6-Trifluorobenzenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 574739312,4,6-Trifluoro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamideYield 21.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 101 mg (0.44 mmol) of 2,4,6-trifluorobenzenesulfonyl chloride in 8 mL of pyridine was stirred at room temperature for 2 hours, and warmed at 70° C. for 18 hours. The mixture was then cooled to room temperature and diluted with 1 N aqueous HCl until acidic and extracted with ethyl acetate. The combined organic layers was washed with 1 N aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, decanted, and concentrated in vacuo. The crude material was crystallized from ether-hexanes to afford 40 mg (21%) of the title compound as a colorless powder. MS: m/z 423 (M+1).

Workup

  1. temperaturewarmed at 70° C. for 18 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers was washed with 1 N aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine
  5. dry with materialdried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated in vacuo
  8. customThe crude material was crystallized from ether-hexanes

Sources & evidence

ORD record
ord-5924dd2054e142daa40287621cf2469e
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Linked notes

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