Sodium Iodide → 2-Chloro-5-iodo-3-((e)-2-(pyridin-4-yl)vinyl)pyridine

HRID 2307762ノート

反応式

HRID 2307762 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.N([O-])=O.[Na+].[Na+].[I-:22].[OH-].[Na+]>OS(O)(=O)=O.O>[Cl:1][C:2]1[C:3](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][C:5]([I:22])=[CH:6][N:7]=1

参加物

7

反応物 4

HCID 5238Sodium Iodide2 回HCID 14798Sodium HydroxideHCID 226076916-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 226074362-Chloro-5-iodo-3-((e)-2-(pyridin-4-yl)vinyl)pyridine収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

実験手順

A solution of Example 21A (1.0 g, 4.3 mmol) in 30% H2SO4 (10 mL) at 0° C. was treated with NaNO2 (386 mg, 5.6 mmol), stirred for 5 hours, treated with a solution of NaI (2.1 g, 14 mmol) in H2O (2 mL), stirred for 2 hours, treated with additional NaI (2.1 g, 14 mmol), stirred for 2 hours, poured into 30% NaOH (aq.) (200 mL) at 0° C. and extracted three times with 10% methanol/ethyl acetate. The combined organic phases were dried (MgSO4), filtered, and concentrated. The residual solid was purified by flash column chromatography on silica gel with 70% ethyl acetate/hexanes to provide the desired product (1.03 g, 70%).

後処理

  1. stirringstirred for 2 hours
  2. stirringstirred for 2 hours
  3. extractionextracted three times with 10% methanol/ethyl acetate
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual solid was purified by flash column chromatography on silica gel with 70% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-1464ef436222472291648f0c9d89c474
出典データセット
uspto-grants-2004_12
特許番号
US06831175B2

反応ノート

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