Sodium Carbonate → HCID 59023593, compound

HRID 1500206Notes

Reaction equation

HRID 1500206 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][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 79799Tolylboronic acid

Product 1

HCID 59023593HCID 59023593, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-5-nitropyridine (5.0 g, 31.5 mmol) and tetrakis(triphenylphosphine)palladium (0.35 g, 0.3 mmol) were added to 1,2-dimethoxyethan (50 ml), then degassed and purged with nitrogen three times under reduced pressure. Under nitrogen atmosphere the mixture was stirred at room temperature for 20 minutes, 4-methylphenylboronic acid (4.29 g, 31.5 mmol) and 2M aqueous sodium carbonate (31.5 ml) were 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. The products were purified by column chromatography to give the title compound (5.4 g, 80.0% yield).

Workup

  1. customdegassed
  2. custompurged with nitrogen three times under reduced pressure
  3. temperaturewas raised to 80° C
  4. customAfter the reaction at 80° C. for 3 hours
  5. temperaturethe mixture was cooled to room temperature
  6. extractionextracted with addition of ethyl acetate and water
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe products were purified by column chromatography

Sources & evidence

ORD record
ord-f52b0714896d4686a285565ad5f79c03
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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