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Cesium carbonate → 2-(2,4-difluorophenoxy)-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

HRID 1454966
ノート
印刷プレビュー

反応式

HRID 1454966 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[OH:35]>CN1C(=O)CCC1.CCOC(C)=O.O>[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[O:35][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 575312262-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

生成物 1

HCID 167499382-(2,4-difluorophenoxy)-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8857
Ethyl Acetate
溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (250 mg, 0.85 mmol) and Cs2CO3 (834 mg, 2.56 mmol) in NMP was added 2,4 difluoro phenol (211 mg, 1.7 mmol). The mixture was heated to 90° C. for 2 hrs until the reaction was complete via LCMS analysis. The reaction was cooled to ambient temperature and diluted with EtOAc and H2O. The aqueous layer was washed with EtOAc and the combined organic layers were washed with 1N NaOH, H2O, brine, dried over MgSO4, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

後処理

  1. temperatureThe reaction was cooled to ambient temperature
  2. washThe aqueous layer was washed with EtOAc
  3. washthe combined organic layers were washed with 1N NaOH, H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

出典と根拠

ORDレコード
ord-d85f7b9965bf4d05ac4d3644d2fd6d68
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07482345B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート