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

HRID 2201811Notes

Reaction equation

HRID 2201811 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-9bd465fd2cc74f68b4ca3b8813d9f532
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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