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Water → 4-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine

HRID 516184
Notes
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Reaction equation

HRID 516184 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[I:11]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.O>CN(C=O)C>[Cl:1][C:2]1[C:7]2[C:8]([I:11])=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 120273N-IodosuccinimideHCID 141143844-chloro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 534128394-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridineYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in WO2007/095223 was dissolved in DMF (7.0 ml). After cooling to 0° C., N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a dark-brown solid (455 mg). Physical properties: m/z [M+H]+ 279.1

Workup

  1. customto separate the organic layer
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5b79e5629ba248c99ea7c71c4731f7a6
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108973B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes