Pyridine → HCID 67235281, compound

HRID 1505378Notes

Reaction equation

HRID 1505378 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[F:10][C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:10][C:11]1[N:16]=[CH:15][C:14]([N:4]2[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]2=[O:7])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6491DimethylhydantoinHCID 2783397(6-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 67235281HCID 67235281, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Two reactions were set up in parallel. For each of them, to a solution of 5,5-dimethyl-2,4-imidazolidinedione (1.5 g, 11.71 mmol) in dry dichloromethane (100 mL), (6-fluoro-3-pyridinyl)boronic acid (1.980 g, 14.05 mmol), copper(II) acetate (2.126 g, 11.71 mmol) and pyridine (1.420 mL, 17.56 mmol) were added. The reaction was left under stirring under air atmosphere at room temperature overnight. The two reaction mixtures were combined and the solid was filtered off. The resulting solution was washed with water (90 mL). The aqueous phase was extracted twice with dichloromethane (twice 90 mL). The organic phases were combined and washed with brine and dried over anhydrous sodium sulphate. Removal of the solvent afforded a residue which was purified by silica gel chromatography (Biotage system, 100 g SNAP column) using as eluent a gradient and cyclohexane/ethyl acetate from 65/35 to 50/50 to afford the title compound as a white solid (1.27 g).

Workup

  1. waitThe reaction was left
  2. customThe two reaction mixtures
  3. filtrationthe solid was filtered off
  4. washThe resulting solution was washed with water (90 mL)
  5. extractionThe aqueous phase was extracted twice with dichloromethane (twice 90 mL)
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customRemoval of the solvent
  9. customafforded a residue which
  10. customwas purified by silica gel chromatography (Biotage system, 100 g SNAP column)

Sources & evidence

ORD record
ord-689cfbf8842d4cea875c501c3de97897
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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