Water → HCID 67970447, compound

HRID 1470716Notes

Reaction equation

HRID 1470716 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.O>O1CCOCC1.CO>[N:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 793484N-((1S)-1-(4-Bromophenyl)ethyl)acetamideHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 67970447HCID 67970447, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Under inert gas atmosphere 181 mg (0.248 mmol) PdCl2(dppf)xCH2Cl2 are added to a mixture of 30.0 g (124 mmol) (S)—N-[1-(4-bromo-phenyl)-ethyl]-acetamide (1.1), 139 mL (279 mmol) 2N sodium carbonate solution and 16.8 g (136 mmol) pyridine-4-boronic acid in 300 mL 1,4-dioxane and 100 mL methanol. The mixture is stirred for 5 d at reflux. After that time, the residue is poured into water (3 L) and extracted with dichloromethane (3×). The combined organic layers are washed with water and dried over magnesium sulphate. The solvent is evaporated and the residue is triturated with acetone and tert-butyl methyl ether.

Workup

  1. temperatureat reflux
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined organic layers are washed with water
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is evaporated
  6. customthe residue is triturated with acetone and tert-butyl methyl ether

Sources & evidence

ORD record
ord-10e3cb22ab8541b1b6d8df09b3e52161
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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