Triethylamine → HCID 23022099, compound

HRID 2409960Notes

Reaction equation

HRID 2409960 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([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)#C.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>[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>[CH3:13][O:12][C:10]1[CH:11]=[C:6]2[C:7]([CH:2]=[C:3]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:5]2)=[CH:8][CH:9]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 1860033-EthynylpyridineHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide

Product 1

HCID 23022099HCID 23022099, compoundYield 54.3%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
50 °C

Procedure

A mixture of 2,2,2-trifluoro-N-(2-iodo-5-methoxyphenyl)acetamide (1.00 g), 3-ethynylpyridine (359 mg), bis(triphenylphosphine) palladium(II) dichloride (61.3 mg), copper(I) iodide (33.1 mg), triethylamine (0.81 mL), and acetonitrile (15 mL) 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 (353 mg). 1H-NMR (CDCl3) δ ppm: 3.87 (3H, s), 6.78-6.86 (2H, m), 6.89-6.94 (1H, m), 7.29-7.43 (1H, m), 7.52 (1H, d, J=8.5 Hz), 7.85-7.94 (1H, m), 8.20-9.10 (3H, m).

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-6a867f3de281433882ce6ca9985705a4
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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