Sodium Carbonate → HCID 10990505, compound

HRID 1633470Notes

Reaction equation

HRID 1633470 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1B(O)O.[NH2:13][C:14]1[C:19](Br)=[N:18][CH:17]=[C:16]([Cl:21])[N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1C=CC=CC=1>[NH2:13][C:14]1[C:19]([C:3]2[CH:4]=[C:5]([Cl:9])[CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])=[N:18][CH:17]=[C:16]([Cl:21])[N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 51065082,3,5-Trichlorophenylboronic acidHCID 179559913-Bromo-6-chloropyrazin-2-amine

Product 1

HCID 10990505HCID 10990505, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A solution of 2,3,5-trichlorobenzeneboronic acid (1.62 g, 7.18×10−3 mole) in absolute ethanol (2.05 ml) was added slowly to a mixture of 2-amino-3-bromo-6-chloropyrazine (1 g, 5.1×10−3 mole) and tetrakis(triphenylphospine)palladium(0) (0.334 g,2.89×1−4 mole) in benzene (10.20 ml)/2M aqueous sodium carbonate (5.50 ml). The mixture was refluxed for 17 hrs. The cooled reaction mixture was evaporated in vacuo and then extracted with chloroform (50 ml). The chloroform layer was washed with water (2×30 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was triturated with 40-60° C. petroleum ether, filtered and dried in vacuo. Yield 0.205 g (14%), M.p. 211-214° C.

Workup

  1. temperatureThe mixture was refluxed for 17 hrs
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo
  4. extractionextracted with chloroform (50 ml)
  5. washThe chloroform layer was washed with water (2×30 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate evaporated down in vacuo
  9. customThe residue was triturated with 40-60° C. petroleum ether
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3ccec39ab5dd48139ceacae71be075f4
Source dataset
uspto-grants-2003_01
Patent number
US06503909B1

Reaction notes

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