2,4-Dimethyl-6-nitrobenzenesulfonyl chloride → HCID 11697910, compound

HRID 1868413Notes

Reaction equation

HRID 1868413 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.[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.[Cl-].[NH4+]>[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1[S:28]([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:29])=[O:30]

Participants

5

Reactant 2

HCID 123831112,4-Dimethyl-6-nitrobenzenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 11697910HCID 11697910, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 150 mg (0.66 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine in 2 mL of pyridine was added 165 mg (0.66 mmol) of 2,4-dimethyl-6-nitrobenzenesulfonyl chloride. The mixture stirred at 80° C. in a sealed tube. After 6 hours, the mixture was diluted with 10 mL of saturated aqueous ammonium chloride solution and extracted with three 10 mL portions of ethyl acetate. The combined ethyl acetate layers were washed with five 10 mL portions of 1 N aqueous HCl, three 10 mL portions of brine, and three 10 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using dichloromethane-hexanes (50-100% gradient). The material from the column was triturated with ether-hexanes to afford 155 mg (53%) of 2,4-dimethyl-6-nitro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide. MS: m/z 442.43 (M+1).

Workup

  1. extractionextracted with three 10 mL portions of ethyl acetate
  2. washThe combined ethyl acetate layers were washed with five 10 mL portions of 1 N aqueous HCl, three 10 mL portions of brine, and three 10 mL portions of saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed on silica gel
  7. customThe material from the column was triturated with ether-hexanes

Sources & evidence

ORD record
ord-dffd76e58c634f259d9f63422db0ef85
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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