Triethylamine → HCID 58408289, compound

HRID 2192281Notes

Reaction equation

HRID 2192281 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH2:18][CH2:17]2.C(N(CC)CC)C>ClCCl>[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 34115665-Bromoindoline

Product 1

HCID 58408289HCID 58408289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.09 g of commercially available 4-cyano-benzenesulfonyl chloride were dissolved in 125 ml dichloromethane. Then 5.0 g 5-Bromo-2,3-dihydro-1H-indole were added followed by 12.2 ml triethylamine. The mixture was stirred at room temperature for thirty minutes. Then the solvent was removed in vacuo. The residue was diluted with 100 ml of ethyl acetate and the mixture washed with 100 ml water and 100 ml saturated NaHCO3 solution. The organic layer was then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by chromatography on silica gel to obtain 5.46 g of 4-(5-Bromo-2,3-dihydro-indole-1-sulfonyl)-benzonitrile.

Workup

  1. customThen the solvent was removed in vacuo
  2. additionThe residue was diluted with 100 ml of ethyl acetate
  3. washthe mixture washed with 100 ml water and 100 ml saturated NaHCO3 solution
  4. dry with materialThe organic layer was then dried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customThe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e8a8bd2f91944294807dce24bdfed64d
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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