Potassium Carbonate → 3-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

HRID 1049246Notes

Reaction equation

HRID 1049246 reaction equation
Br[C:2]1[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][C:2]2[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 904030533-Bromo-2-ethyl-6-nitropyridineHCID 178516507HCID 178516507, compound

Product 1

HCID 904031083-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridineYield 31.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromo-2-ethyl-6-nitropyridine (2.31 g, 10.0 mmol), 2-chloropyridin-4-ol (2.59 g, 20.0 mmol) and K2CO3 (4.15 g, 30.0 mmol) in DMA (20 mL) was sparged with Ar and heated at 105° C. overnight. The mixture was cooled to RT, treated with EtOAc, washed successively with 10% K2CO3 (1×), 5% LiCl (1×) and brine (1×), dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (892 mg, 25%). MS (ESI) m/z: 280.1 (M+H+).

Workup

  1. customwas sparged with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiontreated with EtOAc
  4. washwashed successively with 10% K2CO3 (1×), 5% LiCl (1×) and brine (1×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-d9a42ce2154f4668a84632d884124651
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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