Sodium Carbonate → HCID 22485624, compound

HRID 2181300Notes

Reaction equation

HRID 2181300 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>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.O>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:21]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=2)=[N:9][CH:10]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 27343903,4,5-Trimethoxybenzeneboronic acid

Product 1

HCID 22485624HCID 22485624, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Under nitrogen, tetrakis(triphenylphosphine)palladium (504.6 mg, 0.437 mmol) and a 2.0 M aqueous sodium carbonate (25 mL, 50 mmol) were added to a solution of 2-bromo-5-nitropyridine (2.87 g, 14.1 mmol) and 3,4,5-trimethoxyphenylboronic acid (3.00 g, 14.2 mmol) in ethanol-toluene (1:5, 90 mL), and the resulting mixture was stirred at 70° C. for 12 hours. Water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and crude crystals were obtained. The crude crystals were recrystallized from chloroform-hexane to provide 5-nitro-2-(3,4,5-trimethoxyphenyl)pyridine as yellow needles (melting point: 134.0-136.5° C. )(3.31 g, yield: 81%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. customcrude crystals were obtained
  6. customThe crude crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-0d017588fed84ef485793e52cc15963e
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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