Sodium Carbonate → HCID 18180219, compound

HRID 1383312Notes

Reaction equation

HRID 1383312 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][CH:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1B(O)O>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[NH2:1][C:2]1[C:7]([C:21]2[CH:22]=[C:23]([Cl:27])[CH:24]=[C:25]([Cl:26])[C:20]=2[Cl:19])=[N:6][CH:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 51065082,3,5-Trichlorophenylboronic acid3×HCID 18180200HCID 18180200, compound

Product 1

HCID 18180219HCID 18180219, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolvent3×HCID 178418397HCID 178418397, compoundSolvent

Procedure

A mixture of 2-amino-3-bromo-6-acetamidopyrazine (7.00 g, 0.03 mole) in benzene (60.90 ml) and tetrakis(triphenylphosphine)palladium(0) was stirred under nitrogen at room temperature for 10 minutes. 2M aqueous sodium carbonate (30.24 ml) was added to the mixture followed by a solution of 2,3,5-trichlorobenzene boronic acid (6.83 g, 0.03 mole) in absolute ethanol (7.07 ml) and the mixture refluxed under nitrogen for 17 hrs. A further equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was then added and the mixture refluxed for an additional 7.50 hrs. Finally, another equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was added to the mixture and continued refluxing for 17 hrs. The cooled mixture was evaporated in vacuo. The residue was dissolved in chloroform (150 ml), washed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was purified by ‘flash chromatography’ using chloroform to 98:2 chloroform:methanol as the eluent. Yield 3.02 g (30%), M.p. 200-203° C.

Workup

  1. temperaturethe mixture refluxed under nitrogen for 17 hrs
  2. temperaturethe mixture refluxed for an additional 7.50 hrs
  3. temperaturecontinued refluxing for 17 hrs
  4. customThe cooled mixture was evaporated in vacuo
  5. dissolutionThe residue was dissolved in chloroform (150 ml)
  6. washwashed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated down in vacuo
  10. customThe residue was purified by ‘flash chromatography’

Sources & evidence

ORD record
ord-aa974e05bdff498aa05a03f303a76cf6
Source dataset
uspto-grants-2001_07
Patent number
US06255307B1

Reaction notes

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