5-Bromoindole → HCID 15326267, compound

HRID 964756Notes

Reaction equation

HRID 964756 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]1=[O:18]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:15]1[C:16](=[O:17])[N:12]([CH3:11])[C:13](=[O:18])[CH2:14]1

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 70261N-Methylmaleimide

Product 1

HCID 15326267HCID 15326267, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-bromoindole (5 g, 25.50 mmol) in glacial acetic acid (60 mL) was added N-methylmaleimide (6.1 g, 56.11 mmol) and the resulting mixture was heated to reflux for 4 days. The excess acetic acid was distilled and the crude product dissolved in diethyl ether (500 mL) and washed with saturated sodium bicarbonate (2×100 mL) and brine (3×100 mL). The solvent was evaporated and the residue chromatographed on silica gel using hexane/ethyl acetate (1:1) as the eluent to provide 3-(5-bromo-1H-indol-3-yl)-N-methylsuccinimide (5.85 g, 75%) which was used directly for the next reaction. Yellow solid, m.p. 194°-195° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 days
  3. distillationThe excess acetic acid was distilled
  4. dissolutionthe crude product dissolved in diethyl ether (500 mL)
  5. washwashed with saturated sodium bicarbonate (2×100 mL) and brine (3×100 mL)
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-2d48698423904294aa55fe931c0bc619
Source dataset
uspto-grants-1998_06
Patent number
US05770742

Reaction notes

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