Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate → HCID 67383508、化合物

HRID 335822ノート

反応式

HRID 335822 の反応式
[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]

参加物

5

反応物 2

HCID 67383577Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinateHCID 178418918HCID 178418918、化合物

生成物 1

HCID 67383508HCID 67383508、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3aeb56580dbd4ba3bcab3adac29f6ab5
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

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