Sodium Carbonate → HCID 58219411, compound

HRID 70758Notes

Reaction equation

HRID 70758 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[C:10]1(B(O)O)[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>[C:18]1([C:2]2[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=2)[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 116726802-Chloro-3,5-dimethylpyrazine

Product 1

HCID 58219411HCID 58219411, compoundYield 59%

Reagents, catalysts & solvents 3

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

Procedure

First, into a recovery flask equipped with a reflux pipe were put 2.05 g of 2-chloro-3,5-dimethylpyrazine, 2.48 g of 1-naphthylboronic acid, 1.53 g of sodium carbonate, 0.066 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes, whereby heating was performed. After that, 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 the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. Accordingly, Hdm1npr (a light orange powder, 59% yield), which was the substance to be produced, was obtained. Note that the irradiation with microwaves was performed using a microwaves synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 1 is shown in (a-1) below.

Workup

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes
  3. temperaturewhereby heating
  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. filtrationAfter the drying, the solution was filtered
  8. distillationThe solvent of this solution was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography
  10. customto be produced
  11. customwas obtained
  12. customNote that the irradiation with microwaves
  13. customa microwaves synthesis system (Discover, produced by CEM Corporation)
  14. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-43f207e4f40f43f0acb870f9825ec043
Source dataset
uspto-grants-2014_09
Patent number
US08822682B2

Reaction notes

Loading…