Cesium carbonate → Methyl 3-cyclopropyl-3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-fluorophenyl)propanoate

HRID 709669ノート

反応式

HRID 709669 の反応式
Cl[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:5][CH:4]=1.[CH:23]1([CH:26]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([OH:39])[CH:33]=2)[CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:25][CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:23]1([CH:26]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([O:39][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([C:14]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=4[F:22])=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=3)[CH:33]=2)[CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH2:25]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 1177599996-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridineHCID 117760257Methyl 3-cyclopropyl-3-(4-fluoro-3-hydroxyphenyl)propanoate

生成物 1

HCID 117760040Methyl 3-cyclopropyl-3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-fluorophenyl)propanoate収率 82.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (320 mg) in acetonitrile (30 mL) were added methyl 3-cyclopropyl-3-(4-fluoro-3-hydroxyphenyl)propanoate (220 mg) and cesium carbonate (550 mg), and the mixture was heated under reflux for 15 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (400 mg) as a yellow oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-00dd3c95229c41b998f5e274eb08e94a
出典データセット
uspto-grants-2015_11
特許番号
US09181186B2

反応ノート

読み込み中…