Potassium Carbonate → HCID 18679477, compound

HRID 1633653Notes

Reaction equation

HRID 1633653 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[CH:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 18679499HCID 18679499, compound

Product 1

HCID 18679477HCID 18679477, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

864 mg (4.1 mmol) 1-Phenyl-1H-indol-5-ol in 10 ml acetone were treated with 2.44 g (10 mmol) 1,6-dibromohexane and 2.8 g (20 mmol) K2CO3 at reflux for 4 h. The solution was filtered, concentrated and purified by column chromatography on silica gel with hexane/EtOAc 39:1 to yield 800 mg (52%) 5-(6-Bromo-hexyloxy)-1-phenyl-1H-indole as colorless oil, MS: 371 (M, 1Br).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel with hexane/EtOAc 39:1

Sources & evidence

ORD record
ord-a4b14190ce0b409a8367ae555efe17cb
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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