Sodium Iodide → 2-Chloro-5-iodo-3-((e)-2-(pyridin-4-yl)vinyl)pyridine

HRID 2307762Notes

Reaction equation

HRID 2307762 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.N([O-])=O.[Na+].[Na+].[I-:22].[OH-].[Na+]>OS(O)(=O)=O.O>[Cl:1][C:2]1[C:3](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][C:5]([I:22])=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 5238Sodium Iodide2×HCID 14798Sodium HydroxideHCID 226076916-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 226074362-Chloro-5-iodo-3-((e)-2-(pyridin-4-yl)vinyl)pyridineYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of Example 21A (1.0 g, 4.3 mmol) in 30% H2SO4 (10 mL) at 0° C. was treated with NaNO2 (386 mg, 5.6 mmol), stirred for 5 hours, treated with a solution of NaI (2.1 g, 14 mmol) in H2O (2 mL), stirred for 2 hours, treated with additional NaI (2.1 g, 14 mmol), stirred for 2 hours, poured into 30% NaOH (aq.) (200 mL) at 0° C. and extracted three times with 10% methanol/ethyl acetate. The combined organic phases were dried (MgSO4), filtered, and concentrated. The residual solid was purified by flash column chromatography on silica gel with 70% ethyl acetate/hexanes to provide the desired product (1.03 g, 70%).

Workup

  1. stirringstirred for 2 hours
  2. stirringstirred for 2 hours
  3. extractionextracted three times with 10% methanol/ethyl acetate
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual solid was purified by flash column chromatography on silica gel with 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1464ef436222472291648f0c9d89c474
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

Loading…