Triethylamine → 2-(1H-indol-5-yl)-N-methylethenesulfonamide

HRID 1957726Notes

Reaction equation

HRID 1957726 reaction equation
[CH3:1][NH:2][S:3]([CH:6]=[CH2:7])(=[O:5])=[O:4].Br[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.C(N(CC)CC)C>C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][NH:2][S:3](/[CH:6]=[CH:7]/[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 249055-BromoindoleHCID 21895383N-Methylethenesulfonamide

Product 1

HCID 134757642-(1H-indol-5-yl)-N-methylethenesulfonamideYield 221.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of N-methylethenesulphonamide (45 g), 5-bromoindole (60 g), palladium acetate (0.9 g), triotolylphosphine (18.6 g) and triethylamine (90 mL) in isopropanol (300 mL) was heated at 85° under nitrogen for 18 h. The reaction mixture was cooled to ambient temperature, filtered and the filter cake washed with isopropanol (30 mL). The combined washings and filtrate were concentrated in vacuo to give a yellow-brown solid (160 g). This material was purified by column chromatography on silica gel. Eluting initially with ethyl acetate/cyclohexane (1:1) followed by ethyl acetate provided the product (26.4 g, 36% of theory) as a yellow powder.

Workup

  1. temperaturewas heated at 85° under nitrogen for 18 h
  2. filtrationfiltered
  3. washthe filter cake washed with isopropanol (30 mL)
  4. concentrationThe combined washings and filtrate were concentrated in vacuo

Sources & evidence

ORD record
ord-010ffb3e35184f46b7440175b76d99c4
Source dataset
uspto-grants-1998_07
Patent number
US05786473

Reaction notes

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