Sodium Carbonate → HCID 12034427, compound

HRID 589273Notes

Reaction equation

HRID 589273 reaction equation
Cl[C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[C:14]([CH3:16])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(#N)C>[CH3:9][C:10]1[CH:11]=[C:12]([C:2]2[C:7]([C:12]3[CH:13]=[C:14]([CH3:16])[CH:15]=[C:10]([CH3:9])[CH:11]=3)=[N:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 785752,3-DichloropyrazineHCID 27343493,5-Dimethylphenylboronic acid2×

Product 1

HCID 12034427HCID 12034427, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

First, a mixture of 5.00 g of 2,3-dichloropyrazine, 10.23 g of 3,5-dimethylphenylboronic acid, 7.19 g of sodium carbonate, 0.29 g of bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2), 20 mL of water, and 20 mL of acetonitrile was heated for 60 minutes under argon atmosphere while irradiated with microwaves (2.45 GHz, 100 W). Furthermore, 2.55 g of 3,5-dimethylphenylboronic acid, 1.80 g of sodium carbonate, 0.070 g of PdCl2(PPh3)2, 5 mL of water, and 5 mL of acetonitrile were added, and irradiation with microwaves (2.45 GHz, 100 W) was performed again for 60 minutes so that heating was performed. The mixture was added with water, subjected to extraction with dichloromethane, and purified by column chromatography (developing solvent: hexane:ethyl acetate=5:1 (v/v) and then dichloromethane:ethyl acetate=10:1 (v/v)) to give 2,3-bis(3,5-dimethylphenyl)pyrazine (Hdmdppr) as white powder in 44% yield.

Workup

  1. temperaturewas heated for 60 minutes under argon atmosphere
  2. customwhile irradiated with microwaves (2.45 GHz, 100 W)
  3. customirradiation with microwaves (2.45 GHz, 100 W)
  4. temperatureso that heating
  5. extractionsubjected to extraction with dichloromethane
  6. custompurified by column chromatography (

Sources & evidence

ORD record
ord-0f333820cb074cb3bd5789278412dd53
Source dataset
uspto-grants-2016_01
Patent number
US09231217B2

Reaction notes

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