Sodium Carbonate → HCID 58461049, compound

HRID 2173739Notes

Reaction equation

HRID 2173739 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[C:10]1([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=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>[CH3:8][C:7]1[C:2]([C:23]2[CH:24]=[CH:25][C:20]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][CH:11]=3)=[CH:21][CH:22]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 116726802-Chloro-3,5-dimethylpyrazineHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 58461049HCID 58461049, compoundYield 50%

Reagents, catalysts & solvents 3

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

Procedure

First, into a recovery flask equipped with a reflux pipe were placed 0.74 g of 2-chloro-3,5-dimethylpyrazine, 1.29 g of 4-(1-naphthyl)phenylboronic acid, 0.55 g of sodium carbonate, 0.024 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes, so that heating was performed. Then, the reaction container was cooled to 50° C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and recrystallized using ethyl acetate, whereby Hdm1nppr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 50% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 1 is illustrated in the following (a-1).

Workup

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. customThis reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes
  3. temperatureso that heating
  4. temperatureThen, the reaction container was cooled to 50° C. or less
  5. extractionthe organic layer was extracted with dichloromethane
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customThe solution which had been dried
  9. filtrationwas filtered
  10. distillationThe solvent of this solution was distilled
  11. customrecrystallized
  12. customto be produced
  13. customwas obtained (as a white powder in 50% yield)
  14. customNote that the microwave irradiation
  15. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  16. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-43ba3ceb736e4b339046cba7c0af6888
Source dataset
uspto-grants-2015_06
Patent number
US09056883B2

Reaction notes

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