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Potassium Carbonate → 2'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

HRID 516983
ノート
印刷プレビュー

反応式

HRID 516983 の反応式
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2].Cl[CH2:21][C:22]1[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=3)=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2]
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

6

反応物 3

HCID 11430Potassium CarbonateHCID 534037442-(Chloromethyl)-3,5-difluoropyridineHCID 1177296262'-Acetyl-3-chloro-4-hydroxy-5'-methyl-[1,4]bipyridinyl-2-one

生成物 1

HCID 1177295302'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2′-acetyl-3-chloro-4-hydroxy-5′-methyl-[1,4′]bipyridinyl-2-one of part D (500 mg, 1.7 mmol) in N,N-dimethylformamide (3 mL) was added 2-chloromethyl-3,5-difluoro-pyridine (277 mg, 1.7 mmol), potassium carbonate (590 mg, 4.28 mmol) and 18-crown-6 (10 mg) and the reaction was stirred at 60° C. for 4 h. After cooling the solution was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide alkylated product as a yellow solid (397 mg): MS (ES) m/e 420 (M+H).

後処理

  1. temperatureAfter cooling the solution
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified

出典と根拠

ORDレコード
ord-90c3921b347b445b9224ee3d0a6ce4da
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115089B2

反応ノート

読み込み中…

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