Sodium Carbonate → HCID 58894492, compound

HRID 531891Notes

Reaction equation

HRID 531891 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=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>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 116726802-Chloro-3,5-dimethylpyrazine

Product 1

HCID 58894492HCID 58894492, compoundYield 99%

Reagents, catalysts & solvents 3

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

Procedure

First, to a recovery flask equipped with a reflux pipe were placed 1.03 g of 2-chloro-3,5-dimethylpyrazine, 1.09 g of 4-methoxyphenylboronic acid, 0.76 g of sodium carbonate, 0.032 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the atmosphere in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 10 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 drying, the solution was filtrated. The solvent of this solution was distilled off, whereby a pyrazine derivative Hdmmoppr (dark yellow liquid, yield: 99%), which was a target substance, was obtained. For the irradiation with a microwave, a microwave synthesis system (Discover, manufactured by CEM Corporation) was used. A synthesis scheme of Step 1 is shown by the following (A-1).

Workup

  1. customFirst, to a recovery flask equipped with a reflux pipe
  2. customThis reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 10 minutes
  3. temperatureto be heated
  4. extractionan organic layer was extracted with dichloromethane
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. customAfter drying
  8. filtrationthe solution was filtrated
  9. distillationThe solvent of this solution was distilled off
  10. customwas obtained
  11. customFor the irradiation with a microwave
  12. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  13. customA synthesis scheme of Step 1

Sources & evidence

ORD record
ord-94cc1a5b10a6490bb6366f1ca2cdb3d0
Source dataset
uspto-grants-2016_05
Patent number
US09356250B2

Reaction notes

Loading…