2-Chloro-5-nitropyridine → HCID 86719957, compound

HRID 1500210Notes

Reaction equation

HRID 1500210 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1B(O)O>COCCOC>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 5833222,6-Dimethylphenylboronic acid

Product 1

HCID 86719957HCID 86719957, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-5-nitropyridine (1.0 g, 6.31 mmol), 2,6-dimethylphenylboronic acid (1.42 g, 9.47 mmol) and bis(di-tert-butyl(4-dimethylaminophenylphosphine)dichloropalladium(II) (0.044 g, 0.062 mmol) were added to 1,2-dimethoxyethan (32 ml), degassed and purged with nitrogen three times under reduced pressure. Under nitrogen atmosphere the mixture was stirred at room temperature for 30 minutes, 1M aqueous sodium carbonate (12 ml) was poured in, and the temperature was raised to 80° C. After the reaction at 80° C. for 3 hours, the mixture was cooled to room temperature and extracted with addition of ethyl acetate and water. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography gave the title compound (1.41 g, 98.1%).

Workup

  1. customdegassed
  2. custompurged with nitrogen three times under reduced pressure
  3. addition1M aqueous sodium carbonate (12 ml) was poured in, and the temperature
  4. temperaturewas raised to 80° C
  5. customAfter the reaction at 80° C. for 3 hours
  6. temperaturethe mixture was cooled to room temperature
  7. extractionextracted with addition of ethyl acetate and water
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customPurification by column chromatography

Sources & evidence

ORD record
ord-4a815f6c37254f5785d50d16e9d70c7a
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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