Sodium Carbonate → HCID 136284757, compound

HRID 1255194Notes

Reaction equation

HRID 1255194 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[OH:9])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 2773454(2-Hydroxyphenyl)boronic acid

Product 1

HCID 136284757HCID 136284757, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 2,6-dichloropyrazine (1.00 g, 6.71 mmol), 2-hydroxyphenylboronic acid (972 mg, 7.05 mmol) and trans dichlorobis(triphenylphosphine) palladium (II) (471 mg, 0.671 mmol) were added acetonitrile (20 mL) and sodium carbonate (13.4 mL, 1.0 M in water, 13.4 mmol), and the resulting mixture was degassed by a nitrogen sparge. The reaction flask was equipped with a reflux condenser, then was placed in a pre-heated oil bath (75° C.) and was stirred rapidly. After 5 h, the reaction mixture was allowed to cool to room temperature, then was poured into water and extracted with EtOAc. The organic phase was separated and concentrated in vacuo. Purification by chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 207.6 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 11.64 (s, 1H), 9.11 (s, 1H), 8.53 (s, 1H), 7.85 (dd, J=8.0, 1.5 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.07 (d, J=8.5 Hz, 1H), 6.99 (t, J=8.0 Hz, 1H).

Workup

  1. customthe resulting mixture was degassed by a nitrogen
  2. customsparge
  3. customThe reaction flask was equipped with a reflux condenser
  4. customwas placed in a pre-heated oil bath
  5. temperatureto cool to room temperature
  6. additionwas poured into water
  7. extractionextracted with EtOAc
  8. customThe organic phase was separated
  9. concentrationconcentrated in vacuo
  10. customPurification by chromatography on silica gel (0 to 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-3e6d8680a3d447489b406a581a44527a
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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