Water → HCID 86688749, compound

HRID 2275450Notes

Reaction equation

HRID 2275450 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

Then, 1.21 g of 5-chloro-2,3-bis(3,5-dimethylphenyl)pyrazine obtained in Step 3, 1.10 g of 2,6-dimethylphenylboronic acid, 0.78 g of sodium carbonate, 15 mg of Pd(PPh3)2Cl2, 14 mL of water, and 14 mL of acetonitrile were put into a recovery flask equipped with a reflux pipe, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 3 hours. Here, into the flask were further put 0.55 g of 2,6-dimethylphenylboronic acid, 0.39 g of sodium carbonate, and 7 mg of Pd(PPh3)2Cl2, and the mixture was bubbled with argon for 15 minutes. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 3 hours to be heated. The mixture was suction-filtered and the obtained solid was washed with ethanol. The obtained solid was dissolved in dichloromethane and filtered through a filter aid in which Celite, alumina, and Celite were stacked in that order, so that Hdmdppr-dmp (abbreviation), which was the pyrazine derivative to be produced, was obtained as a white powder in a yield of 89%. A synthesis scheme of Step 4 is shown in (h-4).

Workup

  1. customequipped with a reflux pipe
  2. customthe mixture was bubbled with argon for 15 minutes
  3. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 3 hours
  4. customthe mixture was bubbled with argon for 15 minutes
  5. customThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) again for 3 hours
  6. temperatureto be heated
  7. filtrationThe mixture was suction-filtered
  8. washthe obtained solid was washed with ethanol
  9. dissolutionThe obtained solid was dissolved in dichloromethane
  10. filtrationfiltered through a filter aid in which Celite, alumina, and Celite
  11. customto be produced
  12. customwas obtained as a white powder in a yield of 89%
  13. customA synthesis scheme of Step 4

Sources & evidence

ORD record
ord-c6c684b938994c58b54260db2e0012d9
Source dataset
uspto-grants-2015_09
Patent number
US09127032B2

Reaction notes

Loading…