Bis(pyridine)iodonium tetrafluoroborate → HCID 59200633, compound

HRID 1258426Notes

Reaction equation

HRID 1258426 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9]C)[C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:5][N:4]=1.[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:38]>C1COCC1.C(OCC)(=O)C>[I:38][C:11]1[C:6]2[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=2[O:9][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 59200640HCID 59200640, compound

Product 1

HCID 59200633HCID 59200633, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound S (0.019 g; 0.0705 mmol) and bis(pyridine)iodonium tetrafluoroborate (0.0524 g; 0.14 mmol) in THF (3 ml) was refluxed for 30 min., then diluted to 50 ml with ethyl acetate, washed with saturated Na2S2O5 (3 ml), saturated NaHCO3, dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness under reduced pressure. The residue was purified by column chromatography (silica gel, CH2Cl2) to give pure T (0.0175 g; 65%) 1HNMR (CDCl3) δ 8.2 (s, 1H); 8.04 (d, J=9.0 Hz, 2H); 7.0 (d, J=9.0 Hz, 2H); 6.75 (s, 1H); 3.99 (s, 3H): 3.86 (s, 3H).

Workup

  1. washwashed with saturated Na2S2O5 (3 ml), saturated NaHCO3
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered off
  4. customfiltrate evaporated to dryness under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, CH2Cl2)
  6. customto give pure T (0.0175 g; 65%) 1HNMR (CDCl3) δ 8.2 (s, 1H); 8.04 (d, J=9.0 Hz, 2H); 7.0 (d, J=9.0 Hz, 2H); 6.75 (s, 1H); 3.99 (s, 3H)

Sources & evidence

ORD record
ord-2977c2b374814c8e974997c6b7b02052
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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