1,3-Dibromopropane → HCID 89924264, compound

HRID 1500931Notes

Reaction equation

HRID 1500931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[Br:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:16][CH2:17][CH2:18][CH2:19][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 89924264HCID 89924264, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of ethyl 5-chloro-1H-indole-2-carboxylate (40 g, 0.18 mol), 1,3-dibromo-propane (181 g, 0.90 mol) and potassium carbonate (49.68 g, 0.36 mol) in 500 mL of acetone was heated under reflux for 16 hours. The mixture was concentrated in vacuo to remove the solvent and the residue was diluted with 1000 mL of water, then extracted with ethyl acetate (300 mL×2). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. The residue was purified by flash silica gel chromatography (EtOAc:PE=1:10) to afford 38.5 g of ethyl 1-(3-bromopropyl)-5-chloro-1H-indole-2-carboxylate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the solvent
  5. additionthe residue was diluted with 1000 mL of water
  6. extractionextracted with ethyl acetate (300 mL×2)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash silica gel chromatography (EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-0ea740791dc44e28bb8bb3d3a38623c3
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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