Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate → HCID 67383508, 화합물

HRID 335822노트

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HRID 335822 반응식
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[N:16]=[C:15]([F:17])[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][C:8]=2[C:9]([O:11]C)=O)=[C:4](I)[CH:3]=1.C([Mg]Cl)(C)C>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:22][CH:23]=1)[O:6][C:7]1=[N:16][C:15]([F:17])=[C:14]([Si:18]([CH3:19])([CH3:21])[CH3:20])[CH:13]=[C:8]1[C:9]2=[O:11]

참가 물질

5

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HCID 67383577Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67383508HCID 67383508, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate (2.04 g, 3.89 mmol) was dissolved in dry THF (80 mL) and cooled in a dry ice bath to −78° C. Isopropylmagnesium chloride (2.0 M solution in diethyl ether, 3.89 mL (7.78 mmol) was added and the solution stirred for 15 minutes. The mixture was removed from the cold bath and allowed to slowly warm to RT. Water (100 mL), saturated ammonium chloride (10 mL), and EtOAc (200 mL) were added and the phases mixed and separated. The organics were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (hexane to ethyl acetate gradient) to give 7-bromo-2-fluoro-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridin-5-one.

후처리

  1. customThe mixture was removed from the cold bath
  2. temperatureto slowly warm to RT
  3. additionWater (100 mL), saturated ammonium chloride (10 mL), and EtOAc (200 mL) were added
  4. additionthe phases mixed
  5. customseparated
  6. dry with materialThe organics were dried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe crude was purified

출처 및 근거

ORD 기록
ord-3aeb56580dbd4ba3bcab3adac29f6ab5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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