Sodium Carbonate → HCID 18180204, compound

HRID 1358981Notes

Reaction equation

HRID 1358981 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](Cl)=[N:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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>[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]=[CH:16][N:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2762242-Amino-3-chloropyrazineHCID 51065082,3,5-Trichlorophenylboronic acid

Product 1

HCID 18180204HCID 18180204, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A solution of 2,3,5-trichlorobenzeneboronic acid (1.54 g, 6.82 mmol) in absolute ethanol (1-5 ml) was added slowly to a mixture of 2-amino-3-chloropyrazine (0.589 g, 4.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.299 g, 0.259 mmol) in benzene (10.5 ml)/2M aqueous sodium carbonate (4.54 ml). The mixture was refluxed for 17 hours. The cooled reaction mixture was partitioned between water and ethylacetate (50 ml). The organic layer was washed with water (2×30 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography using chloroform to 0.5%methanol/chloroform as the eluent. The product was then crystallised from 40-60 petrol. Yield 0.15 g, 12% M.p. 142-143° C.

Workup

  1. temperatureThe mixture was refluxed for 17 hours
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethylacetate (50 ml)
  4. washThe organic layer was washed with water (2×30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography
  8. customThe product was then crystallised from 40-60 petrol

Sources & evidence

ORD record
ord-b6a7664913514436aa7a0ca2e9607209
Source dataset
uspto-grants-2003_07
Patent number
US06599905B2

Reaction notes

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