3-{1-[6-(2,4-Difluorophenyl)pyridin-2-yl]-2-oxobut-3-yn-1-yl}-4-fluorobenzonitrile → 3-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-4-fluorobenzonitrile

HRID 1360683ノート

反応式

HRID 1360683 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH:15]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[F:28])[C:23]#[N:24])[C:16](=[O:19])[C:17]#[CH:18])[CH:12]=[CH:11][CH:10]=1>CN1C(=O)CCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[C:13]([CH:12]=[CH:11][CH:10]=1)=[C:15]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[C:23]#[N:24])[C:16](=[O:19])[CH:17]=[CH:18]2

参加物

3

反応物 1

HCID 577003623-{1-[6-(2,4-Difluorophenyl)pyridin-2-yl]-2-oxobut-3-yn-1-yl}-4-fluorobenzonitrile

生成物 1

HCID 160647573-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-4-fluorobenzonitrile

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a solution of 3-{1-[6-(2,4-difluorophenyl)pyridin-2-yl]-2-oxobut-3-yn-1-yl}-4-fluorobenzonitrile (From Step E above, 24 g, 63.8 mmol) in NMP was heated to 90° C. for ½ hour. LCMS analysis revealed the reaction was complete and the reaction was poured into ice water (4 L). After stirring for 12 h, the solid precipitate was collected by filtration. The solid was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH). The aqueous filtrate was extracted with EtOAc. The organic layer was washed with H2O (4×), brine (2×), dried over MgSO4, and condensed in vacuo. The crude residue was purified using silica gel chromatography (CH2Cl2/EtOAc/MeOH). A combined 7.8 g of the title compound was collected.

後処理

  1. filtrationthe solid precipitate was collected by filtration
  2. customThe solid was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH)
  3. extractionThe aqueous filtrate was extracted with EtOAc
  4. washThe organic layer was washed with H2O (4×), brine (2×)
  5. dry with materialdried over MgSO4, and condensed in vacuo
  6. customThe crude residue was purified
  7. customA combined 7.8 g of the title compound was collected

出典と根拠

ORDレコード
ord-2f9454ceb9c44dd1a50b5bbe4b0c3db0
出典データセット
uspto-grants-2011_02
特許番号
US07879875B2

反応ノート

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