Potassium Carbonate → 2-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

HRID 1049249Notes

Reaction equation

HRID 1049249 reaction equation
F[C:2]1[C:3]([CH3:11])=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:19][C:15]1[CH:14]=[C:13]([O:12][C:2]2[C:3]([CH3:11])=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 591847405-Fluoro-4-methyl-2-nitropyridineHCID 178516507HCID 178516507, compound

Product 1

HCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridineYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-4-methyl-2-nitropyridine (2.75 g, 17.6 mmol), 4-hydroxy-2-chloropyridine (3.42 g, 26.4 mmol) and K2CO3 (2.44 g, 17.6 mmol) in DMF (40 mL) was heated at 80° C. for 16 h. The mixture was cooled to RT, diluted with water (400 mL) and extracted with EtOAc (3×100 mL). The combined organics were washed with water (100 mL) and 10% aq. LiCl (80 mL), dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (3.0 g, 64%) as an off-white solid. MS (ESI) m/z: 266.0 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with water (100 mL) and 10% aq. LiCl (80 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-49037ed341d04150a829f3fba3116d87
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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