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 1360683노트

반응식

HRID 1360683 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f9454ceb9c44dd1a50b5bbe4b0c3db0
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879875B2

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