Water → N-Ethyl-2-(4-pyridin-4-yl-phenyl)-propionamide

HRID 409720Notes

Reaction equation

HRID 409720 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.[CH2:16]([NH:18][C:19](=[O:29])[CH:20]([C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1)[CH3:21])[CH3:17].O>O1CCOCC1.CO>[CH2:16]([NH:18][C:19](=[O:29])[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([C:10]2[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=2)=[CH:24][CH:23]=1)[CH3:21])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 66693450N-Ethyl-2-(4-iodo-phenyl)-propionamide

Product 1

HCID 86686108N-Ethyl-2-(4-pyridin-4-yl-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Under inert gas atmosphere 36 mg (0.049 mmol) PdCl2(dppf)xCH2Cl2, 28 mL (56 mmol) 2N sodium carbonate solution and 3.35 g (27.2 mmol) pyridine-4-boronic acid are added to 7.50 g (24.7 mmol) N-ethyl-2-(4-iodo-phenyl)-propionamide (V1.1) in 45 mL 1,4-dioxane and 15 mL methanol. The mixture is stirred for 2 d at reflux. After that time, water is added and the mixture is extracted with EtOAc (2×). The combined organic layers are washed with water and 150 mL 1N HCl are added. The aq. layer is separated, filtered and alkalized with 1N NaOH. The precipitate is filtered off and dried.

Workup

  1. temperatureat reflux
  2. extractionthe mixture is extracted with EtOAc (2×)
  3. washThe combined organic layers are washed with water and 150 mL 1N HCl
  4. additionare added
  5. customThe aq. layer is separated
  6. filtrationfiltered
  7. filtrationThe precipitate is filtered off
  8. customdried

Sources & evidence

ORD record
ord-b833042ccb9849a9828e8ccd1c602d33
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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