Ethyl Acetate → HCID 70926915, compound

HRID 467514Notes

Reaction equation

HRID 467514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([OH:13])=[O:12].[H-].[Na+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19].CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:6]=[C:5]2[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 178402465-Chloro-1H-indole-3-carboxylic acid

Product 1

HCID 70926915HCID 70926915, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

110 ml of a solution containing 10 g of 5-chloro-1H-indole-3-carboxylic acid (commercial) in DMF is added dropwise to a mixture of 4.50 g of NaH (60% in oil) in 400 ml of DMF at −10° C. After it returns to RT, it is stirred for 1 hour. The reaction mixture is cooled to −20° C. 4.86 ml of methyl bromoacetate is added dropwise, it is returned to RT for a period of 5 hours and is stirred for 15 hours. The reaction mixture is added to 1 L of EtOAc/1N HCl mixture, the organic phase is collected and the aqueous phase is extracted with EtOAc. The organic phases are combined, washed with water and with brine, then dried over Na2SO4 and evaporated to dryness. 8.9 g of the expected compound is obtained in the form of a white powder.

Workup

  1. customreturns to RT
  2. waitit is returned to RT for a period of 5 hours
  3. stirringis stirred for 15 hours
  4. customthe organic phase is collected
  5. extractionthe aqueous phase is extracted with EtOAc
  6. washwashed with water and with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-fd066be2dd164c88ae3f9211285acbbe
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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