Sodium Carbonate → 3,5-Dimethyl-2-(6-phenylnaphthalen-2-yl)pyrazine

HRID 2173744Notes

Reaction equation

HRID 2173744 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:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21](B(O)O)[CH:20]=[CH:19]3)[CH:15]=[CH:14][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:21]2[CH:20]=[CH:19][C:18]3[C:23](=[CH:24][CH:25]=[C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:17]=3)[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 57539613(6-Phenylnaphthalen-2-yl)boronic acid

Product 1

HCID 584610453,5-Dimethyl-2-(6-phenylnaphthalen-2-yl)pyrazineYield 82%

Reagents, catalysts & solvents 3

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

Procedure

First, into a recovery flask equipped with a reflux pipe were placed 0.24 g of 2-chloro-3,5-dimethylpyrazine, 0.41 g of 6-phenylnaphthalene-2-boronic acid, 0.18 g of sodium carbonate, 0.008 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 30 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, whereby Hdm6p2npr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 82% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-4).

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 30 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. customto be produced
  12. customwas obtained (as a white powder in 82% yield)
  13. customNote that the microwave irradiation
  14. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  15. customThe synthesis scheme of Step 4

Sources & evidence

ORD record
ord-c34ecc62869048e6abda4d0e166894b9
Source dataset
uspto-grants-2015_06
Patent number
US09056883B2

Reaction notes

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