Pyridine → 1-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

HRID 130486Notes

Reaction equation

HRID 130486 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>C1COCC1>[C:19]1([S:25]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 2531171-(2,3-Dihydro-1H-indol-5-yl)ethan-1-one

Product 1

HCID 141129561-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,3-Dihydro-1H-indol-5-yl)-ethanone (0.200 g, 1.24 mmol) was dissolved in THF (2 ml) before pyridine (0.303 ml, 3.75 mmol) was added, leaving a yellow solution. The benzenesulfonyl chloride (0.220 g, 1.24 mmol) was then added, as a solid, with stirring. The reaction mixture was stirred at 40 C for 5 h. The mixture was cooled and the THF and pyridine were removed in vacuo. The desired sulfonamide (0.310 g, 1.02 mmol, 82%) was recrystallized from ethyl acetate and hexanes. It had LC-MS (ES+): 302 [MH]+ m/e

Workup

  1. additionwas added
  2. customleaving a yellow solution
  3. stirringThe reaction mixture was stirred at 40 C for 5 h
  4. temperatureThe mixture was cooled
  5. customthe THF and pyridine were removed in vacuo

Sources & evidence

ORD record
ord-1a284aaa23ec4f8f9029bbecc9b61d57
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

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