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

HRID 2278896Notes

Reaction equation

HRID 2278896 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 28.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromo-2-ethyl-6-nitropyridine (3.168 g, 13.71 mmol), 2-chloro-4-hydroxypyridine (3.55 g, 27.4 mmol) and K2CO3 (5.69 g, 41.1 mmol) in DMA (25 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, 5% LiCl, then brine, 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 (1.102 g, 28%). MS (ESI) m/z: 280.0 (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, 5% LiCl
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-8407629d10a149e38caf52422532398e
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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