Chlorosuccinimide → HCID 59494548, compound

HRID 872047Notes

Reaction equation

HRID 872047 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH:9]1[C:17]2[CH:16]=[C:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:14]=[CH:13][C:12]=2[CH:11]=[CH:10]1>ClCCl>[Cl:1][C:11]1[C:12]2[CH:13]=[N:14][C:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][C:17]=2[NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57763153HCID 57763153, compound

Product 1

HCID 59494548HCID 59494548, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (514 mg) was added to a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridin-6-carboxylate (800 mg) in dichloromethane (16 ml) at room temperature and the mixture was stirred at the room temperature for 3 hours. The reaction mixture was concentrated in vacuo and the resulted residue was dissolved in tetrahydrofuran. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo to give a crude product of tert-butyl 3-chloro-1H-pyrrolo[3,2-c]pyridin-6-carboxylate (1.06 g) as an orange powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulted residue was dissolved in tetrahydrofuran
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90395f72db4a4983bcbbadcc6e1f18b6
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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