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

HRID 875419Notes

Reaction equation

HRID 875419 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 (332 mg, 2.5 mmol) and stirred at room temperature for about 5 hours. The reaction mixture was diluted with dichloromethane and washed with aq. sodium hydrogen carbonate solution, brine, dried over anhydrous sodium sulphate and concentrated. Purification by silica gel (100-200) column chromatography using methanol and dichloromethane gradient as eluent afforded 3-chloro-1H-pyrrolo[3,2-c]pyridine (103 mg, 40%).

Workup

  1. washwashed with aq. sodium hydrogen carbonate solution, brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated
  4. customPurification by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-40b75ea3865c4815ab9cce19b8ccd94c
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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