Water → HCID 86688749, compound

HRID 589275Notes

Reaction equation

HRID 589275 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)[C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)=[N:6][CH:7]=1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1[C:2]1[N:3]=[C:4]([C:16]2[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:5]([C:8]2[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 86688747HCID 86688747, compound

Product 1

HCID 86688749HCID 86688749, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Next, a mixture of 1.21 g of 5-chloro-2,3-bis(3,5-dimethylphenyl)pyrazine, 1.10 g of 2,6-dimethylphenylboronic acid, 0.78 g of sodium carbonate, 15 mg of PdCl2(PPh3)2, 14 mL of water, and 14 mL of acetonitrile was degassed by bubbling argon for 15 minutes and irradiated with microwaves (2.45 GHz, 100 W) for 3 hours. To the mixture were further added 0.55 g of 2,6-dimethylphenylboronic acid, 0.39 g of sodium carbonate, and 7 mg of PdCl2(PPh3)2, and the mixture was degassed by bubbling argon for 15 minutes and heated again by irradiating with microwaves for 6 hours. The mixture was suction-filtered, and the resulting solid was washed with ethanol. The obtained solid was dissolved in dichloromethane, which was followed by filtration through Celite, alumina, and Celite in this order. The filtrate was concentrated to give 5-(2,6-dimethylphenyl)-2,3-bis(3,5-dimethylphenyl)pyrazine as white powder in 89% yield. Explanation of the following reactions is omitted because they are the same as those in Example 5.

Workup

  1. customwas degassed
  2. customby bubbling argon for 15 minutes
  3. customirradiated with microwaves (2.45 GHz, 100 W) for 3 hours
  4. customthe mixture was degassed
  5. customby bubbling argon for 15 minutes
  6. temperatureheated again
  7. customby irradiating with microwaves for 6 hours
  8. filtrationThe mixture was suction-filtered
  9. washthe resulting solid was washed with ethanol
  10. dissolutionThe obtained solid was dissolved in dichloromethane
  11. filtrationwhich was followed by filtration through Celite, alumina, and Celite in this order
  12. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bd5699ac892b4fef92deaf6c19e3a8d6
Source dataset
uspto-grants-2016_01
Patent number
US09231217B2

Reaction notes

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