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

HRID 982009Notes

Reaction equation

HRID 982009 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][NH:12][S:13]([CH:16]=[CH2:17])(=[O:15])=[O:14].C(N(CC)CC)C>C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2](/[CH:17]=[CH:16]/[S:13]([NH:12][CH3:11])(=[O:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 249055-BromoindoleHCID 21895383N-Methylethenesulfonamide

Product 1

HCID 134757642-(1H-indol-5-yl)-N-methylethenesulfonamideYield 28.9%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromoindole (6.6 g), N-methylethenesulphonamide (5.1 g) palladium (II) acetate (75 mg), tri-o-tolylphosphine (0.2 g), triethylamine (12 ml), and acetonitrile (5 ml) was heated at 100° in an autoclave for 3 h. The reaction mixture was cooled and partitioned between hydrochloric acid (1N, 300 ml) and ethyl acetate (2×150 ml). The combined extracts were dried, (Na2SO4) and evaporated in vacuo to give an oil which was purified by `flash` chromatography (Q, 7 cm dia. col.) to give the title compound as a solid (2.3 g) m.p. 164√-166°.

Workup

  1. temperaturewas heated at 100° in an autoclave for 3 h
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between hydrochloric acid (1N, 300 ml) and ethyl acetate (2×150 ml)
  4. customThe combined extracts were dried
  5. custom(Na2SO4) and evaporated in vacuo
  6. customto give an oil which
  7. customwas purified by `flash` chromatography (Q, 7 cm dia. col.)

Sources & evidence

ORD record
ord-dbdd133000904a6aa455d06e7c3ac5a1
Source dataset
uspto-grants-1991_02
Patent number
US04994483

Reaction notes

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