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

HRID 1868416Notes

Reaction equation

HRID 1868416 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[S:11](Cl)(=[O:13])=[O:12].[F:15][C:16]([F:30])([F:29])[CH:17]([NH2:28])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[S:11]([NH:28][CH:17]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[C:16]([F:15])([F:29])[F:30])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 189816282,4-Dichloro-6-methoxybenzenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 116984292,4-Dichloro-6-methoxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamideYield 59.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 50 mg (0.18 mmol) of 2,4-dichloro-6-methoxybenzenesulfonyl chloride in 4 mL of pyridine was added 42 mg (0.19 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine. The mixture stirred for 6 hours at room temperature and was then diluted with 10 mL of ethyl acetate and washed with four 30 mL portions of 10% acetic acid, two 30 mL portions of saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, decanted and concentrated in vacuo. The crude material was purified by filtering through a pad of silica eluting with ether. The material from the pad was dissolved in ether, and precipitated by slow evaporation which afforded 50 mg (57%) of the title compound as a bright yellow powder. MS: m/z 467 (M+1).

Workup

  1. washwashed with four 30 mL portions of 10% acetic acid, two 30 mL portions of saturated aqueous sodium bicarbonate solution, and brine
  2. dry with materialdried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified
  6. filtrationby filtering through a pad of silica eluting with ether
  7. dissolutionThe material from the pad was dissolved in ether
  8. customprecipitated by slow evaporation which

Sources & evidence

ORD record
ord-3ff6bd3b149548969d127a798231de58
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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