Pyridine → HCID 67235281、化合物

HRID 1505378ノート

反応式

HRID 1505378 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 67235281HCID 67235281、化合物収率 48.6%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-689cfbf8842d4cea875c501c3de97897
出典データセット
uspto-grants-2015_12
特許番号
US09216967B2

反応ノート

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