Cesium carbonate → N-{2-[4-(3,4-Dimethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76199Notes

Reaction equation

HRID 76199 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:25]#[CH:26])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>C1COCC1.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.[Cu]I>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:25]#[C:26][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 36164214-Ethynyl-1,2-dimethoxybenzeneHCID 66611344N-(1-(4-Iodophenyl)propan-2-YL)acetamide

Product 1

HCID 66613362N-{2-[4-(3,4-Dimethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 0.40 g (1.32 mmol) N-[2-(4-iodo-phenyl)-1-methyl-ethyl]-acetamide (I52.1) and 0.21 g (1.32 mmol) 3,4-dimethoxyphenyl acetylene in 5 mL THF are added 0.10 g (0.13 mmol) bis-(triphenylphosphin)-palladium(II)-chlorid, 26.0 mg (0.14 mmol) CuI and 0.56 g (1.72 mmol) Cs2CO3. The mixture is stirred in a sealed tube at r.t. over night. The reaction mixture is poured onto sat. aq. NaHCO3 solution and extracted with EtOAc (2×). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by HPLC (ACN/MeOH/TFA).

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by HPLC (ACN/MeOH/TFA)

Sources & evidence

ORD record
ord-027e1d3eeb164d9fb13b5943452b1879
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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