Sodium Carbonate → HCID 58219440, compound

HRID 531892Notes

Reaction equation

HRID 531892 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1B(O)O.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>[CH:18]1[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:17]=1[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 116726802-Chloro-3,5-dimethylpyrazine

Product 1

HCID 58219440HCID 58219440, compoundYield 56%

Reagents, catalysts & solvents 3

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

Procedure

First, to a recovery flask equipped with a reflux pipe were placed 2.25 g of 2-chloro-3,5-dimethylpyrazine, 2.71 g of 2-naphthylboronic acid, 1.67 g of sodium carbonate, 0.072 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 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 and the residue obtained by distillation was purified by silica gel column chromatography using dichloromethane as a developing solvent. In this way, Hdm2npr (a light orange powder, yield: 56%), 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 in the following (B-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. customthe residue obtained by distillation
  11. customwas purified by silica gel column chromatography
  12. customwas obtained
  13. customFor the irradiation with a microwave
  14. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  15. customA synthesis scheme of Step 1

Sources & evidence

ORD record
ord-3abb64a9425d4dce95d29d929990387b
Source dataset
uspto-grants-2016_05
Patent number
US09356250B2

Reaction notes

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