Potassium Carbonate → HCID 86703277, compound

HRID 2409956Notes

Reaction equation

HRID 2409956 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1I)=O.C[Si](C)(C)C#C[C:21]1[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.[Cl-].[Na+].O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(#N)C.C(N(CC)CC)C>[CH3:13][O:12][C:10]1[CH:11]=[C:6]2[C:7]([CH:2]=[C:3]([C:21]3[CH:25]=[C:24]([CH3:26])[S:23][CH:22]=3)[NH:5]2)=[CH:8][CH:9]=1

Participants

11

Reactant 4

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamideHCID 86703276HCID 86703276, compound

Product 1

HCID 86703277HCID 86703277, compoundYield 63.7%

Reagents, catalysts & solvents 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2,2,2-trifluoro-N-(2-iodo-5-methoxyphenyl)acetamide (1.00 g), trimethyl(5-methylthiophen-3-ylethynyl)silane (845 mg), bis(triphenylphosphine) palladium(II) dichloride (61 mg), copper(I) iodide (33 mg), triethylamine (0.81 mL), and acetonitrile (15 mL) was added tetrabutylammonium fluoride in tetrahydrofuran solution (1 mol/L, 4.4 mL) at 50° C. This mixture was stirred at 50° C. for 1 hour. Then, potassium carbonate (801 mg) was added thereto, followed by stirring at 50° C. overnight. To the reaction mixture was added saturated brine, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (449 mg). 1H-NMR (CDCl3) δ ppm: 2.53 (3H, d, J=1.0 Hz), 3.86 (3H, s), 6.53-6.59 (1H, m), 6.77 (1H, dd, J=2.3, 8.6 Hz), 6.84-6.89 (1H, m), 7.01-7.11 (2H, m), 7.46 (1H, d, J=8.6 Hz), 7.94-8.16 (1H, br).

Workup

  1. stirringby stirring at 50° C. overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4094b8e81a804684b69062bf461ebb0f
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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