Triethylamine → HCID 69096929, compound

HRID 2400274Notes

Reaction equation

HRID 2400274 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][C:3]=1[NH:11][C:12](=O)[C:13](F)(F)F.[C:18]1(C#C)[CH:23]=[CH:22]C=[CH:20][CH:19]=1.[CH2:26](N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.[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.C(#N)C>[Cl:10][C:5]1[CH:4]=[C:3]2[C:2]([CH:26]=[C:12]([C:13]3[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=3)[NH:11]2)=[CH:7][C:6]=1[O:8][CH3:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 86665746HCID 86665746, compound

Product 1

HCID 69096929HCID 69096929, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of N-(2-bromo-5-chloro-4-methoxyphenyl)-2,2,2-trifluoroacetamide (512 mg), phenylacetylene (0.254 mL), copper(I) iodide (17.5 mg), triethylamine (0.549 mL), and acetonitrile (12.3 mL) was added bis(triphenylphosphine) palladium(II) dichloride (32.5 mg). The mixture was stirred at 120° C. for 2 hours under microwave irradiation. The reaction mixture was left to cool. To the reaction mixture was added potassium carbonate (532 mg). The mixture was stirred at 120° C. for 2 more hours under microwave irradiation. The reaction mixture was left to cool, and filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (255 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 6.70-6.80 (1H, m), 7.13 (1H, s), 7.30-7.50 (4H, m), 7.60-7.70 (2H, m), 8.00-8.40 (1H, br).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. stirringThe mixture was stirred at 120° C. for 2 more hours under microwave irradiation
  4. waitThe reaction mixture was left
  5. temperatureto cool
  6. filtrationfiltered through Celite (registered trademark)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b746733e528b4324aa072d371910b41f
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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