1-Ethynyl-4-methoxybenzene → N-Ethyl-2-[4-(4-methoxy-phenylethynyl)-phenyl]-propionamide

HRID 330842Notes

Reaction equation

HRID 330842 reaction equation
[CH2:1]([NH:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)#[CH:16]>C(#N)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CCOC(C)=O>[CH2:1]([NH:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:16]#[C:15][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)[CH3:6])[CH3:2]

Participants

7

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 66693450N-Ethyl-2-(4-iodo-phenyl)-propionamide

Product 1

HCID 56929774N-Ethyl-2-[4-(4-methoxy-phenylethynyl)-phenyl]-propionamide

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.99 mmol) N-Ethyl-2-(4-iodo-phenyl)-propionamide (XVIII.1) are added to 148 μL (1.14 mmol) 1-ethynyl-4-methoxybenzene in 8 mL ACN under inert gas atmosphere. 276 μL (1.99 mmol) TEA as base, 6 mg (0.03 mmol) copper(I)iodide and 42 mg (0.060 mmol) bis(triphenylphosphine)palladium(II)chloride as catalyst are added and the mixture is stirred at rt under inert gas atmosphere for 5 h. After that time, the mixture is diluted with EtOAc, washed with saturated ammonium chloride solution and brine, and the organic layer is dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50).

Workup

  1. washwashed with saturated ammonium chloride solution and brine
  2. dry with materialthe organic layer is dried over sodium sulphate
  3. customThe solvent is evaporated
  4. customthe residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50)

Sources & evidence

ORD record
ord-1dc9197ce3d74b39bd9f65ad4711d3f5
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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