5-Azaindole → 3-Chloro-1H-pyrrolo[3,2-c]pyridine

HRID 875418Notes

Reaction equation

HRID 875418 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[Cl:10]N1C(=O)CCC1=O>ClCCl>[Cl:10][C:3]1[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 92205-AzaindoleHCID 31398Chlorosuccinimide

Product 1

HCID 247292153-Chloro-1H-pyrrolo[3,2-c]pyridineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1H-pyrrolo[3,2-c]pyridine (200 mg, 1.69 mmol) in dichloromethane (10 ml) was treated with N-chlorosuccinimide (339 mg, 2.5 mmol) and stirred at room temperature for 5 hours. The reaction mixture was diluted with dichloromethane and washed with aqueous sodium hydrogen carbonate solution, brine, dried over anhydrous sodium sulfate and concentrated. Purification from silica gel column chromatography using methanol and dichloromethane gradient afforded 3-chloro-1H-pyrrolo[3,2-c]pyridine (98 mg, 40%).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate solution, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customPurification from silica gel column chromatography

Sources & evidence

ORD record
ord-33c1d451262c4cfea337a15c8de83587
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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