Chlorosuccinimide → HCID 22311004, compound

HRID 902869Notes

Reaction equation

HRID 902869 reaction equation
[F: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.[Cl:16]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Cl:16][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][C:6]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

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

Ethyl 5-fluoroindole-2-carboxylate (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 to the solution under ice cooling. The mixture was stirred at room temperature for 18 hours, and the reaction mixture was diluted with ethyl acetate and successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride. The resultant organic layer was then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to obtain the title compound (1.9 g).

Workup

  1. washsuccessively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride
  2. dry with materialThe resultant organic layer was then dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ccf9137ce60a4df6ad27e04ae9495a00
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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