3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[(5-Fluoro-2-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile

HRID 1712094ノート

反応式

HRID 1712094 の反応式
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[C:21]([O:24][CH3:25])=[CH:22][CH:23]=1>C1COCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:1]([OH:2])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:19]=1

参加物

4

反応物 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178491810HCID 178491810、化合物

生成物 1

HCID 592052073-{3-[(5-Fluoro-2-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 3-fluoro-6-methoxyphenylmagnesium bromide in THF (0.3 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 3-{3-[(5-fluoro-2-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

後処理

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-a4b12d8013754451ad8621fdf924a71c
出典データセット
uspto-grants-2010_09
特許番号
US07790895B2

反応ノート

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