Chlorosuccinimide → HCID 22311004, compound

HRID 2104396Notes

Reaction equation

HRID 2104396 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([F:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[Cl:16]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[Cl:16])=[CH:12][C:11]([F:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 22311004HCID 22311004, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-Fluoroindole-2-carboxylic acid ethyl ester (2.0 g) was dissolved in N,N-dimethylformamide (20 mL), and a solution of N-chlorosuccinimide (1.4 g) in N,N-dimethylformamide (10 mL) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, and the diluted mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), to thereby give the title compound (1.9 g).

Workup

  1. washthe diluted mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5e77052415e34a989a5e7541ffd69443
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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