2,6-Dichloro-4-(trifluoromethyl)benzenesulfonyl chloride → 2,6-Dichloro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]4-trifluoromethylbenzenesulfonamide

HRID 1868411Notes

Reaction equation

HRID 1868411 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.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([Cl:28])[C:19]=1[S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1.Cl>[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[C:20]([Cl:28])[C:19]=1[S:29]([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:31])=[O:30]

Participants

5

Reactant 2

HCID 27368692,6-Dichloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 115696752,6-Dichloro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]4-trifluoromethylbenzenesulfonamideYield 18%

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 137 mg (0.44 mmol) of 2,6-dichloro-4-(trifluoromethyl)benzenesulfonyl 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 cooled to room temperature and diluted with 1 M HCl until acidic and extracted with ethyl acetate. The combined organic layers were 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 (18%) of the title compound as a colorless powder. MS: m/z 505 (M), 507 (M+2).

Workup

  1. temperaturewarmed at 70° C. for 18 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were 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-854f082c218246f88b373ea953b367e1
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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