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Methyl iodide → N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide

HRID 53524
ノート
印刷プレビュー

反応式

HRID 53524 の反応式
[H-].[Na+].[Br:3][C:4]1[C:9]([NH:10][C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=1.[CH3:22]I>CS(C)=O>[Br:3][C:4]1[C:9]([N:10]([CH3:22])[C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=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

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10617311N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide

生成物 1

HCID 10737014N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

Sodium hydride (0.3 g of a 50% dispersion in mineral oil) was added to dimethylsulfoxide (10 ml) and warmed to 50° C. After cooling the mixture to room temperature, N-(2-bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide (2.0 g) was added and the resulting solution was stirred for 10 min. Methyl iodide (0.4 ml) was then added and the mixture was stirred for 30 min. The reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml) was then added. The organic phase was washed with water (4×100 ml), dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2) to give 1.9 g of the title compound, suitable for use in the next reaction.

後処理

  1. temperatureAfter cooling the mixture to room temperature
  2. stirringthe mixture was stirred for 30 min
  3. customThe reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml)
  4. additionwas then added
  5. washThe organic phase was washed with water (4×100 ml)
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2)

出典と根拠

ORDレコード
ord-eb4d12397c644580a5eb2f8ae600c6ad
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05620974

反応ノート

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