Sodium Carbonate → HCID 22485538, compound

HRID 2181288Notes

Reaction equation

HRID 2181288 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=1>O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 276852,5-DichloropyridineHCID 27343903,4,5-Trimethoxybenzeneboronic acid

Product 1

HCID 22485538HCID 22485538, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under argon, 3,4,5-trimethoxyphenylboronic acid (5.05 g, 24.0 mmol), dichloro[1,2-bis(diphenylphosphino)ethane]palladium (574.0 mg, 1.00 mmol) and a 2.0 M aqueous sodium carbonate (20 mL, 40 mmol) were added to a solution of 2,5-dichioropyridine (2.95 g, 20.0 mmol) in ethanol-toluene (1:5, 54.0 mL). After stirring at 100° C. for 3 hours, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as a colorless crystalline powder (melting point: 61.0-63.0° C.)(4.13 g, yield 73%)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bac48a143de14bbb8dd6ccf5967584a4
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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