5-Bromoindole → 5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

HRID 609745Notes

Reaction equation

HRID 609745 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[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.N1CCCC1>C(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[C:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH:14]=1

Participants

5

Reactant 3

HCID 249055-BromoindoleHCID 31268PyrrolidineHCID 740491-Methyl-4-piperidone

Product 1

HCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromoindole (4.31 g, 22 mmol), 1-methyl4-piperidone (2.46 mL, 20 mmol) and pyrrolidine (17 mL, 200 mmol) were mixed in ethanol (30 mL) and refluxed for 72 hours. The mixture was cooled to room temperature and the resulting solid, collected by filtration, washed with methanol and dried to provide as 5-bromo-3-(1,2,3,6-tetrahydro-1-methyl4-pyridinyl)-1H-indole white solid (4.40 g, 76%). mp>230° C. dec.

Workup

  1. temperaturerefluxed for 72 hours
  2. filtrationthe resulting solid, collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-2234b9be39f84503b3d937c98ddbd88c
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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