1,3-Dibromopropane → HCID 53735845, compound

HRID 2298237Notes

Reaction equation

HRID 2298237 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:17][CH2:16][CH2:15][Br:14])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 53735845HCID 53735845, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In a flask was dissolved indole-3-carboxylic acid methyl ester (2.0 g, 11.4 mmole) and 1,3-dibromopropane (11.5 g, 57 mmol) in 15 mL of DMF. To this solution was added cesium carbonate (5.5 g, 17 mmol). The flask was sealed and the content was stirred at 40° C. overnight. The solution was then partitioned between ether and water. The ethereal phase was washed twice with water and once with brine and was finally evaporated. The residue was purified on silica (heptane-ethyl acetate 4:1), to give 2.2 g (75%) of the sub-title compound.

Workup

  1. customThe flask was sealed
  2. customThe solution was then partitioned between ether and water
  3. washThe ethereal phase was washed twice with water and once with brine
  4. customwas finally evaporated
  5. customThe residue was purified on silica (heptane-ethyl acetate 4:1)

Sources & evidence

ORD record
ord-a333962d357f45f09be825e49422a6af
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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