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

HRID 2258133Notes

Reaction equation

HRID 2258133 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.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[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

7

Reactant 3

HCID 8471TriethylamineHCID 249055-BromoindoleHCID 21895383N-Methylethenesulfonamide

Product 1

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

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of N-methylethenesulphonamide (45 g), 5-bromoindole (60 g), palladium acetate (0.9 g), tri-o-tolylphosphine (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-ef64e549f04b4b789e3f45a8f6905dc3
Source dataset
uspto-grants-1997_08
Patent number
US05659040

Reaction notes

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