Chlorosuccinimide → tert-butyl 3-chloro-1H-indole-5-carboxylate

HRID 1821950Notes

Reaction equation

HRID 1821950 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17]N1C(=O)CCC1=O>CO>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[Cl:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11183550Tert-butyl 1H-indole-5-carboxylate

Product 1

HCID 11615783tert-butyl 3-chloro-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 389 mg (1.79 mmol) tert-butylindole-5-carboxylate in 12 ml methanol is mixed with 335 mg (2.50 mmol) N-chlorosuccinimide and stirred at room temperature overnight. The methanol is removed by rotation and the resulting residue is taken up in 15 ml ethyl acetate. The organic phase is washed twice with 1M sodium hydrogen carbonate solution, dried on sodium sulfate and concentrated by rotation. Column chromatographic processing of the residue on silica gel (flow agent: hexane/ethyl acetate 9:1) yields a solid.

Workup

  1. customThe methanol is removed by rotation
  2. washThe organic phase is washed twice with 1M sodium hydrogen carbonate solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by rotation
  5. customColumn chromatographic processing of the residue on silica gel (flow agent: hexane/ethyl acetate 9:1) yields a solid

Sources & evidence

ORD record
ord-76ae2a6d0eac44f6963cccf40ccba4c3
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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