1-Fluoro-2,6-dichloropyridinium Triflate → HCID 58349833, compound

HRID 1426663Notes

Reaction equation

HRID 1426663 reaction equation
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-]S(C(F)(F)[F:20])(=O)=O.F[N+]1C(Cl)=CC=CC=1Cl>C(#N)C.O1CCCC1.C(=O)([O-])O.[Na+]>[F:20][C:9]1[C:10]([CH:13]=[O:14])=[CH:11][NH:12][C:8]=1[C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 27373111-Fluoro-2,6-dichloropyridinium TriflateHCID 58349828HCID 58349828, compound

Product 1

HCID 58349833HCID 58349833, compoundYield 15.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-(2-Fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (660 mg) was dissolved in acetonitrile (30 mL) and tetrahydrofuran (30 mL), 1-fluoro-2,6-dichloropyridinium triflate (1.32 g) was added, and the mixture was stirred for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:2→3:7) to give the title compound as pale-yellow crystals (yield 110 mg, 15%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:2→3:7)

Sources & evidence

ORD record
ord-970ef6308c754e219258abd8596786ee
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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