Dichloromethane → 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

HRID 386408Notes

Reaction equation

HRID 386408 reaction equation
[I:1]Cl.ClCCl.[Cl:6][C:7]1[N:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1>CN1CCCC1=O.N1C=CC=CC=1>[Cl:6][C:7]1[N:8]=[C:9]2[C:15]([I:1])=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24640Iodine chlorideHCID 457896382-Chloro-5H-pyrrolo[2,3-B]pyrazine

Product 1

HCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazineYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

A 1M solution of iodine chloride in dichloromethane (4 ml, 4 mmol) was added dropwise to an ice-cold solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (4) in N-methylpyrrolidone (residual from previous step) and pyridine (5 ml). The reaction mixture was stirred for 60 minutes at 0° C. and then was concentrated in vacuo. The residue was purified by flash chromatography, using as eluent pentane/EtOAc 0% to 50%, to give the title compound (820 mg, 75% over two steps). 1H NMR (DMSO-d6) 8.2 (1H, s), 8.4 (1H, s). MS (ES+): 280

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e163a31e3dd94cdaacbd12802624c337
Source dataset
uspto-grants-2013_02
Patent number
US08372835B2

Reaction notes

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