1,3-Dibromopropane → HCID 20098374, compound

HRID 1165231Notes

Reaction equation

HRID 1165231 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].[Br:26][CH2:27][CH2:28][CH2:29]Br>CC(C)=O>[Br:26][CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 13787417HCID 13787417, compound

Product 1

HCID 20098374HCID 20098374, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2 g of N-(2-hydroxyphenyl)-1H-indol-4-carboxamide and 2.18 g of potassium carbonate in 20 ml of acetone was admixed with 3.2 ml of 1,3-dibromopropane and the mixture was refluxed for 90 minutes and was filtered. The solvent was evaporated under reduced pressure and the residue was chromatographed over silica (eluant: chloroform/ethyl acetate/triethylamine 6:3:1 to obtain 2.37 g of N-[2-[3-bromopropoxy)phenyl]-1H-indole-4-carboxamide melting at 145° C.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. filtrationwas filtered
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was chromatographed over silica (eluant

Sources & evidence

ORD record
ord-6c3baad17c794270addd44f0216bfaf0
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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