Hexane → HCID 45257525, compound

HRID 1670350Notes

Reaction equation

HRID 1670350 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:14]=[C:15]([F:19])[CH:16]=[CH:17][CH:18]=1.[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.O1CCCC1>[F:19][C:15]1[CH:14]=[C:13]([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:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 140821-Bromo-3-fluorobenzeneHCID 2439072,3-DiphenylpyrazineHCID 178418339Butyllithium

Product 1

HCID 45257525HCID 45257525, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

First, 7.5 mL (1.58 mol/L) of hexane solution of n-butyllithium was added dropwise to a mixed solution of 1.49 g of 3-bromofluorobenzene and 11 mL of tetrahydrofuran at −78° C. under an atmosphere of nitrogen, and stirred for 30 minutes, keeping the temperature at −78° C. The obtained solution was added dropwise to a mixed solution, which was cooled with ice, of 2.45 g of 2,3-diphenylpyrazine and 20 mL of tetrahydrofuran, and stirred for 1 hour at room temperature. Water was added to this mixture and an organic layer was extracted using ethyl acetate as an extraction solvent. The obtained organic layer was washed with water and dried with anhydrous magnesium sulfate. After drying, the solution was filtrated. 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. In this way, Hdppr-3FP (an orange powder, yield: 8%), which was a target substance was obtained. A synthetic scheme of Step 1 is shown by a following (c-2).

Workup

  1. customat −78° C
  2. additionThe obtained solution was added dropwise to a mixed solution, which
  3. stirringstirred for 1 hour at room temperature
  4. extractionan organic layer was extracted
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter drying
  8. filtrationthe solution was filtrated
  9. distillationThe solvent of the solution was distilled off
  10. customthe residue obtained by distillation
  11. customwas purified by silica gel column chromatography
  12. customwas obtained

Sources & evidence

ORD record
ord-218b177a2897428e93629b002404a65f
Source dataset
uspto-grants-2011_08
Patent number
US07993494B2

Reaction notes

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