2-Ethoxy-4-iodopyridine → N-{2-[4-(2-Ethoxy-pyridin-4-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76200Notes

Reaction equation

HRID 76200 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].[CH2:16]([O:18][C:19]1[CH:24]=[C:23](I)[CH:22]=[CH:21][N:20]=1)[CH3:17]>C(#N)C.[Cu]I>[CH2:16]([O:18][C:19]1[CH:24]=[C:23]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=2)[CH:22]=[CH:21][N:20]=1)[CH3:17]

Participants

5

Reactant 2

HCID 666107722-Ethoxy-4-iodopyridineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Product 1

HCID 66610737N-{2-[4-(2-Ethoxy-pyridin-4-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

To 100 mg (0.50 mmol) N-[2-(4-ethynyl-phenyl)-1-methyl-ethyl]-acetamide (I58.2) and 124 mg (0.50 mmol) 2-ethoxy-4-iodo-pyridine (I6.1) in 5.00 mL ACN are added 20.3 mg (0.03 mmol) 1,1′-bis[diphenylphosphino]ferrocenepalladium dichloride dichloromethane complex (1:1), 4.83 mg (0.03 mmol) CuI and 0.16 mL (1.16 mmol) TEA. The mixture is stirred at r.t. over night, then poured onto water and extracted with DCM. The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is purified by column chromatographie (silica gel; PE/EtOAc 1/1→EtOAc 100%).

Workup

  1. additionpoured onto water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer is dried with MgSO4
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified by column chromatographie (silica gel; PE/EtOAc 1/1→EtOAc 100%)

Sources & evidence

ORD record
ord-c850e99305e04996985a3dd93b2ef0ef
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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