Ethyl chloroacetate → HCID 49651889, compound

HRID 1777731Notes

Reaction equation

HRID 1777731 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C([O-])([O-])=O.[K+].[K+].C([O:20][C:21](=[O:24])[CH2:22]Cl)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:22][C:21]([OH:24])=[O:20]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 1383634-Methoxy-1H-indole

Product 1

HCID 49651889HCID 49651889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyindole (294 mg) in DMF (10 mL) was added K2CO3 (829 mg). After 10 min stirring, ethylchloroacetate (0.426 mL) was added. The reaction mixture was stirred overnight at 120° C., was allowed to cool down and was filtered off. The solid was washed with DCM and the filtrate was concentrated in vacuo. After CC (silica gel, EA/MeOH 9/1) followed by preparative HPLC (I), the resulting material was dissolved in 1M NaOH/THF (20 mL, 1/1). The mixture was stirred at RT overnight, neutralized with 1M HCl (8 mL) and concentrated to dryness. The residue was taken up in DCM and the resulting suspension was filtered off. The filtrate was evaporated in vacuo to afford 340 mg of beige powder. LC-MS (D): tR=0.76 min; [M+H]+: 206.1.

Workup

  1. stirringThe reaction mixture was stirred overnight at 120° C.
  2. temperatureto cool down
  3. filtrationwas filtered off
  4. washThe solid was washed with DCM
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionthe resulting material was dissolved in 1M NaOH/THF (20 mL, 1/1)
  7. stirringThe mixture was stirred at RT overnight
  8. concentrationconcentrated to dryness
  9. filtrationthe resulting suspension was filtered off
  10. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-71a07e25744844be976cdb5d345ba1ae
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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