Sodium Carbonate → 2-Chloro-6-(2-Furyl)Pyrazine

HRID 1357580Notes

Reaction equation

HRID 1357580 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.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:10]2[O:9][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 2734357Furan-2-boronic acid

Product 1

HCID 181868472-Chloro-6-(2-Furyl)Pyrazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,2-Dimethoxyethane (130 mL) was added to a mixture of tetrakis(triphenylphosphine)palladium (0) (0.93 g, 0.80 mmol) and 2,6-dichloropyrazine (2.55 g, 17.1 mmol). After 5 min of stirring at room temperature, furan-2-boronic acid (1.91 g, 17.1 mmol) followed by aqueous Na2CO3 (30 mL; 2 M) were added. The mixture was heated at reflux for 1 h [TLC monitoring by SiO2/n-hexane/ethyl acetate (90:10)]. The layers were separated and the light brownish water layer was extracted with dichloromethane (2×200 mL). The combined organic layers were dried (K2CO3), filtered and concentrated in vacuo. The brown-yellow oil obtained was purified by silica gel chromatography (18.5×4 cm) eluting with n-hexane/ethyl acetate (90:10). This furnished 1.47 g (48%) of the title compound as a light yellow solid. HRMS m/z calcd for C8H5ClN2O (M)+ 180.0090, found 180.0092. Anal. (C8H5ClN2O) 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 dichloromethane (2×200 mL)
  5. dry with materialThe combined organic layers were dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe brown-yellow oil obtained
  9. customwas purified by silica gel chromatography (18.5×4 cm)
  10. washeluting with n-hexane/ethyl acetate (90:10)

Sources & evidence

ORD record
ord-7ac3d17bf3d24867885a0a594ec44c83
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

Loading…