Water → HCID 90403315, compound

HRID 1049233Notes

Reaction equation

HRID 1049233 reaction equation
[I:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].O>CC(N(C)C)=O>[Cl:10][C:11]1[CH:16]=[C:15]([O:9][C:5]2[C:6]([CH3:8])=[N:7][C:2]([I:1])=[CH:3][CH:4]=2)[CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 335152,4-DichloropyridineHCID 121942112-Methyl-3-hydroxy-6-iodopyridine

Product 1

HCID 90403315HCID 90403315, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-iodo-2-methylpyridin-3-ol (6.8 g, 28.9 mmol), 2,4-dichloro pyridine (8.56 g, 57.9 mmol) and K2CO3 (4.00 g, 28.9 mmol) in DMA (50 mL) was heated at 110° C. for 16 h under argon. The mixture was cooled to RT, treated with H2O, extracted with EtOAc (2×) and the combined organics were washed with H2O, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-((2-chloropyridin-4-yl)oxy)-6-iodo-2-methylpyridine (7.35 g, 73%) as a white solid. MS (ESI) m/z: 346.9 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (2×)
  3. washthe combined organics were washed with H2O
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-d81fffc025e44941917c26b209ac541f
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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