Sodium Carbonate → HCID 18186818, compound

HRID 1357582Notes

Reaction equation

HRID 1357582 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[S:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 581760Thiophene-3-boronic acid

Product 1

HCID 18186818HCID 18186818, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,2-Dimethoxyethane (120 mL) was added to a mixture of tetrakis(triphenylphosphine)palladium (0) (0.87 g, 0.75 mmol) and 2,6-dichloropyrazine (2.43 g, 16.3 mmol). After 15 min of stirring at room temperature, thiophene-3-boronic acid (2.09 g, 16.3 mmol) followed by aqueous Na2CO3 (2 M; 25 mL) were added. The mixture was heated at reflux for 2 h [TLC monitoring by SiO2/n-hexane/ethyl acetate (85:15)]. The layers were separated and the light brownish water layer was extracted with ether (2×100 mL). The combined organic layers were dried (K2CO3), filtered and concentrated in vacuo. The brownish oil obtained was purified by silica gel chromatography (18×5 cm) eluting with n-hexane/ethyl acetate (85:15). This furnished 1.46 g (45%) of the title compound as an off-white solid. HRMS m/z calcd for C8H5ClN2S (M)+ 195.9862, found 195.9868. Anal. (C8H5ClN2S) C, H, N.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. customThe layers were separated
  4. extractionthe light brownish water layer was extracted with ether (2×100 mL)
  5. dry with materialThe combined organic layers were dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe brownish oil obtained
  9. customwas purified by silica gel chromatography (18×5 cm)
  10. washeluting with n-hexane/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-39056170e12c4dd79f27f00ef6bd7542
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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