Tetrahydrofuran → HCID 57782445, compound

HRID 1670351Notes

Reaction equation

HRID 1670351 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.O1CCCC1.C([Li])CCC.[C:20]1([C:26]2[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:30][CH:29]=[CH:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.CCCCCC>[F:9][C:4]1[CH:3]=[C:2]([C:29]2[N:30]=[C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:27][CH:28]=2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 1363131-Bromo-3,5-difluorobenzeneHCID 2439072,3-DiphenylpyrazineHCID 178418339Butyllithium

Product 1

HCID 57782445HCID 57782445, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

First, to a mixed solution of 4.02 g of 1-bromo-3,5-difluorobenzene and 40 mL of tetrahydrofuran was added dropwise 14 mL (1.61 mol/L) of hexane solution of n-butyllithium at −78° C. under an atmosphere of nitrogen, and the solution was stirred for 2 hours at −78° C. In addition, to this mixed solution was added 4.03 g of 2,3-diphenylpyrazine in five steps at −78° C., and the temperature of the solution was raised to room temperature. Water was added to this mixture and an organic layer was extracted using diethylether as an extraction solvent. The obtained organic layer was washed with water and dried with anhydrous magnesium sulfate. The solution after drying was filtrated, and the magnesium sulfate was removed. The solvent of the solution was distilled off and the residue obtained by distillation was purified by silica gel column chromatography using dichloromethane as a developing solvent, so that a pyrazine derivative Hdppr-3,5FP (an orange powder, yield: 4%), which was a target substance was obtained. A synthetic scheme of Step 2 is shown by a following (c-3).

Workup

  1. temperaturethe temperature of the solution was raised to room temperature
  2. extractionan organic layer was extracted
  3. washThe obtained organic layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solution after drying
  6. filtrationwas filtrated
  7. customthe magnesium sulfate was removed
  8. distillationThe solvent of the solution was distilled off
  9. customthe residue obtained by distillation
  10. customwas purified by silica gel column chromatography
  11. customwas obtained

Sources & evidence

ORD record
ord-5e79884f8bef4be18dc16b282d77baf3
Source dataset
uspto-grants-2011_08
Patent number
US07993494B2

Reaction notes

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