Triethylamine → HCID 69096929, compound

HRID 1191662Notes

Reaction equation

HRID 1191662 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.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=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 178419050HCID 178419050, compoundCatalystHCID 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 (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 irradiation of microwave. The reaction mixture was allowed to cool to ambient temperature. Potassium carbonate (532 mg) was added to the reaction mixture. The mixture was stirred at 120° C. for additional 2 hours under irradiation of microwave. The reaction mixture was allowed to cool to ambient temperature and filtered through celite (registered trademark). The filtrate was concentrated under reduced pressure and the residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (255 mg).

Workup

  1. temperatureto cool to ambient temperature
  2. stirringThe mixture was stirred at 120° C. for additional 2 hours under irradiation of microwave
  3. temperatureto cool to ambient temperature
  4. filtrationfiltered through celite (registered trademark)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0e67d89c9dc44c9c9ba6d763dda37c70
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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