5-Bromoindole → HCID 43340386, compound

HRID 2067703Notes

Reaction equation

HRID 2067703 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.[C:11]1([CH2:17][CH2:18][C:19](N2C3C=CC=CC=3N=N2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[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:19](=[O:20])[CH2:18][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 249055-BromoindoleHCID 786030HCID 786030, compound

Product 1

HCID 43340386HCID 43340386, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromoindole (1.0 g) in methylene chloride (10 ml), 1-(3-phenylpropanoyl)-1H-1,2,3-benzotriazole (1.28 g) was added. While stirring under ice cooling, a solution of titanium(IV) chloride (1.11 ml) in methylene chloride (5.0 ml) was added and the mixture was stirred at room temperature for 5 days. To the reaction solution, ice water (50 ml) was added, the mixture was stirred for a while, then the organic layer was separated and successively washed with water and brine and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (methylene chloride:methanol=19:1 to 4:1) to afford the above-identified compound (1.22 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 days
  2. stirringthe mixture was stirred for a while
  3. customthe organic layer was separated
  4. washsuccessively washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off in vacuo
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (methylene chloride:methanol=19:1 to 4:1)

Sources & evidence

ORD record
ord-2d9aef998d8c48ec9093f060b4a04b6c
Source dataset
uspto-grants-2012_10
Patent number
US08293781B2

Reaction notes

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