Iodine → 3-Iodo-1-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine

HRID 659939

Reaction equation

HRID 659939 reaction equation
[CH3:1][N:2](C)[C:3]1[C:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.[I:18]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[I:18][C:9]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:3]2[N:2]([CH3:1])[C:10]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 68429284Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amine

Product 1

HCID 684305853-Iodo-1-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridineYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 g (4.4 mmoles) of Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amine are dissolved in 60 mL of dichloromethane under argon atmosphere. A solution of 2.27 g of iodine (8.9 mmoles) in 35 mL of dichloromethane is added dropwise in the reaction mixture at 0° C. The reaction mixture is allowed to reach room temperature and further stirred for 4 hours. The reaction mixture is then poured into a solution sodium thiosulfate and extracted with dichloromethane. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is purified by chromatography on silica gel (ethylacetate) to give 600 mg of 3-Iodo-1-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine as brown solid.

Workup

  1. customto reach room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solid residue after concentration
  6. customis purified by chromatography on silica gel (ethylacetate)

Sources & evidence

ORD record
ord-0f92119da96a421f9e3b88b7f28a0351
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Linked notes

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