Sodium Carbonate → HCID 58518561, compound

HRID 1618887Notes

Reaction equation

HRID 1618887 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]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(#N)C>[C:10]1([CH3:9])[CH:11]=[CH:12][CH:13]=[C:14]([C:2]2[C:7]([C:14]3[CH:15]=[C:10]([CH3:9])[CH:11]=[CH:12][CH:13]=3)=[N:6][CH:5]=[CH:4][N:3]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 785752,3-DichloropyrazineHCID 27339503-Tolylboronic acid

Product 1

HCID 58518561HCID 58518561, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

First, 2.39 g of 2,3-dichloropyrazine, 4.51 g of 3-methylphenyl boronic acid, 3.74 g of sodium carbonate, 0.17 g of bis(triphenylphosphine)palladium(II)dichloride (abbr.: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile were put in a round-bottomed flask with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 3 hours and 40 minutes to be heated. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off to obtain 2,3-di-m-tolylpyradine (a white powder, yield: 80%). A synthetic scheme of Step 1 is represented by (E4-1) below.

Workup

  1. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 3 hours and 40 minutes
  2. temperatureto be heated
  3. extractionan organic layer was extracted with dichloromethane
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the drying, the solution was filtrated
  7. distillationThe solvent of this solution was distilled off
  8. customto obtain 2,3-di-m-tolylpyradine (a white powder, yield: 80%)

Sources & evidence

ORD record
ord-264d634279f04c6b8e196968028c4c97
Source dataset
uspto-grants-2014_07
Patent number
US08772082B2

Reaction notes

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