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

HRID 2307762노트

반응식

HRID 2307762 반응식
[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

참가 물질

7

반응물 4

HCID 5238Sodium Iodide2회HCID 14798Sodium HydroxideHCID 226076916-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amineHCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1464ef436222472291648f0c9d89c474
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831175B2

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