N-Iodosuccinimide → 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine

HRID 1778693Notes

Reaction equation

HRID 1778693 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[N:20][NH:21][C:15]=2[CH:14]=1.[I:22]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([I:22])=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 867228206-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1784934546-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridineYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At r.t. to a stirring solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridine (0.62 g, 1.9 mmol) in methylene chloride (10 mL) was added N-iodosuccinimide (0.47 g, 2.1 mmol). The mixture was stirred at r.t. for 2 h. It was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product 0.50 g.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-805f9de4858e429ca9be7525f240b187
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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