HCID 88880313, compound → HCID 70664579, compound

HRID 468649Notes

Reaction equation

HRID 468649 reaction equation
BrC1C=CC(N/[N:9]=[CH:10]/[CH:11]=[N:12]/[NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[F:21])=C(F)C=1>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[N:9]=[CH:10][CH:11]=[N:12]2)=[C:15]([F:21])[CH:16]=1

Participants

4

Reactant 1

HCID 88880313HCID 88880313, compound

Product 1

HCID 70664579HCID 70664579, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 1140TolueneSolvent

Procedure

Copper (II) trifluoromethanesulfonate (218 mg, 0.60 mmol) was added to a slurry of (1E,2E)-ethanedial bis[(4-bromo-2-fluorophenyl)hydrazone] (2.61 g, 6.04 mmol) in toluene (25 mL). The reaction was heated to reflux and stirred at this temperature overnight. The reaction was allowed to cool and was filtered through celite, and the filter pad was washed with EtOAc (100 mL). The combined filtrates were washed with 1 N aq HCl (3×100 mL), water (100 mL), and brine (100 mL) and then dried (MgSO4), filtered and concentrated. The crude product was purified via flash chromatography using a Varian SF25-40 g column and an eluent of EtOAc in hexanes (0-50%) to afford the title compound as a yellow solid (1.08 g, 73.9%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.44 (ddd, 1H) 7.47-7.54 (m, 1H) 7.76 (t, 1H) 7.90 (s, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationwas filtered through celite
  5. washthe filter pad was washed with EtOAc (100 mL)
  6. washThe combined filtrates were washed with 1 N aq HCl (3×100 mL), water (100 mL), and brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified via flash chromatography

Sources & evidence

ORD record
ord-c84eb94f65214e8da6fe720ecc670148
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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