Iodide Ion → HCID 69507850, compound

HRID 1375652Notes

Reaction equation

HRID 1375652 reaction equation
C([SnH2][C:6]1[O:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1)(C)(C)C.I[C:17]1[CH:18]=[C:19](/[CH:23]=[CH:24]/[CH2:25][OH:26])[CH:20]=[CH:21][CH:22]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[I-].[F-].[K+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:26][CH2:25]/[CH:24]=[CH:23]/[C:19]1[CH:18]=[C:17]([C:6]2[O:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 30165Iodide IonHCID 521585Tris(furan-2-yl)phosphaneHCID 522689Potassium FluorideHCID 58787323HCID 58787323, compoundHCID 87867900HCID 87867900, compound

Product 1

HCID 69507850HCID 69507850, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The tributyltin reagent from Example 1C (665 μL, 1.83 mmol) was added under nitrogen atmosphere to a mixture of alcohol from Example 1B (433 mg, 1.66 mmol), tris(dibenzylideneacetone)-dipalladium(0) (76 mg, 0.083 mmol), tri-2-furylphosphine (39 mg, 0.166 mmol), and cupper(I) iodide (32 mg, 0.166 mmol) in DMF (7 mL). The reaction mixture was stirred at ambient temperature for 30 minutes. Aqueous potassium fluoride was added to the mixture and the resulting suspension was filtered through celite and washed with ethyl acetate. The filtrate was taken up in ethyl acetate and water. The organic phase was washed with brine (×3), dried (MgSO4), filtered and concentrated under reduced pressure and purified by flash chromatography on silica gel with hexane/ethyl acetate (1:1) to provide the titled compound (353 mg). MS (ESI(+)) m/e 291 (M+18)+; 1H NMR (500 MHz, DMSO-d6) δ 8.05(t, J=1.7 Hz, 1H), 7.80 (dt, J1=1.7 Hz, J2=7.5 Hz, 1H), 7.60 (dt, J1=1.7 Hz, J2=7.5 Hz, 1H), 7.57 (s, 1H), 7.51(t, J=7.5 Hz, 1H), 6.63–6.59 (m, 2H), 4.94 (t, J=5.4 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 4.19–4.14(m, 2H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationthe resulting suspension was filtered through celite
  2. washwashed with ethyl acetate
  3. washThe organic phase was washed with brine (×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography on silica gel with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-2ad8b7def229499bba3e7af2d350ff14
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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