Sodium Carbonate → HCID 67283736, compound

HRID 1183756Notes

Reaction equation

HRID 1183756 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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.ClCCl.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:20]2[CH:21]=[CH:22][C:17]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:18][CH:19]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 116726802-Chloro-3,5-dimethylpyrazine

Product 1

HCID 67283736HCID 67283736, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

First, into a recovery flask equipped with a reflux pipe were placed 1.35 g of 2-chloro-3,5-dimethylpyrazine, 2.02 g of 4-phenoxyphenylboronic acid, 1.00 g of sodium carbonate, 0.043 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air inside the flask was replaced with argon. Heating was performed by microwave irradiation (2.45 GHz, 100 W) of this reaction container for 10 minutes, so that reaction occurred. After that, water was added to this reaction solution, and extraction with dichloromethane was carried out. A solution of the obtained extract was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. After the solvent of this solution was distilled, the obtained residue was washed with methanol, so that the pyrazine derivative which was the object of the synthesis, Hdmpoppr, was obtained (a white powder in a yield of 89%). Note that a microwave synthesis system (Discover, produced by CEM Corporation) was used for the microwave irradiation. The synthesis scheme of Step 1 is illustrated in the following formulae (e).

Workup

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. temperatureHeating
  3. customwas performed by microwave irradiation (2.45 GHz, 100 W) of this reaction container for 10 minutes, so that reaction
  4. extractionA solution of the obtained extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter the drying, the solution was filtered
  8. distillationAfter the solvent of this solution was distilled
  9. washthe obtained residue was washed with methanol, so that the pyrazine derivative which
  10. customthe object of the synthesis, Hdmpoppr
  11. customwas obtained (a white powder in a yield of 89%)
  12. customNote that a microwave synthesis system (Discover, produced by CEM Corporation)
  13. customwas used for the microwave irradiation
  14. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-2e98e1cebeeb48c899fa6b9f6e1324e0
Source dataset
uspto-grants-2014_03
Patent number
US08664383B2

Reaction notes

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