Cesium carbonate → 7-(2,4-difluorophenoxy)-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

HRID 1454979ノート

反応式

HRID 1454979 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:4]([CH:5]=[CH:6][C:7](=[O:20])[C:8]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[OH:29].CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.C(OCC)(=O)C.Cl[Cu]>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[O:29][C:2]1[CH:11]=[CH:10][C:9]2[N:4]([CH:5]=[CH:6][C:7](=[O:20])[C:8]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 1230512,4-DifluorophenolHCID 575312307-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

生成物 1

HCID 167496317-(2,4-difluorophenoxy)-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

To a solution of 7-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one (100 mg, 0.3 mmole) was added 2,4-difluorophenol (0.06 ml, 0.6 mmole), 2,2,6,6-tetramethylheptane-3,5-dione (0.007 ml, 0.03 mmole), CuCl (15 mg, 0.15 mmole) and cesium carbonate (195 mg, 0.6 mmole) in NMP. The mixture was heated to 120° C. until the reaction completed. The mixture was diluted with ethyl acetate, washed with 1N HCl, 1N NaOH, brine, dried over MgSO4, and concentrated to yield crude material. The crude material was purified by silica gel chromatography (CH2Cl2/acetone) to yield the title compound.

後処理

  1. washwashed with 1N HCl, 1N NaOH, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto yield crude material
  5. customThe crude material was purified by silica gel chromatography (CH2Cl2/acetone)

出典と根拠

ORDレコード
ord-0e56735d6a7f4e929fb19d752382a4ed
出典データセット
uspto-grants-2009_01
特許番号
US07482345B2

反応ノート

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