Ethyl Bromide → (Imidazo[1,2-a]pyridin-5-yl)oxoacetic Acid Ethyl Ester

HRID 1725374ノート

反応式

HRID 1725374 の反応式
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.BrCC.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[CH2:18]([O:17][C:15](=[O:16])[C:14]([C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1)=[O:20])[CH3:19]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 7268Diethyl OxalateHCID 130372415-Bromoimidazo(1,2-a)pyridine

生成物 1

HCID 67340610(Imidazo[1,2-a]pyridin-5-yl)oxoacetic Acid Ethyl Ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

Add Mg turnings (0.25 g, 9.95 mmol) to a solution of 5-Bromoimidazo[1,2-a]pyridine (1.5 g, 7.65 mmol) in tetrahydrofuran (20 ml). Heat the reaction to 60° C. and add bromoethane (1.2 ml, 11.1 mmol). Reflux for another 0.5 hours, cool and cannula dropwise into a solution of diethyl oxalate (5 ml) in tetrahydrofuran (5 ml) at −15° C. Stir at −15° C. for 0.5 hours and at room temperature for 0.5 hours. Quench the reaction by adding pH 7 buffer, extract into ethyl acetate, wash with saturated sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate:hexane:methanol gradient gives the title compound as a light brown oil.

後処理

  1. temperatureHeat
  2. customthe reaction to 60° C.
  3. temperatureReflux for another 0.5 hours
  4. temperaturecool
  5. customat −15° C
  6. customQuench
  7. customthe reaction
  8. additionby adding pH 7 buffer
  9. extractionextract into ethyl acetate
  10. washwash with saturated sodium chloride
  11. dry with materialdry over magnesium sulfate
  12. concentrationconcentrate under reduced pressure
  13. customPurification by flash chromatography
  14. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-dc0151f42b45403abb5f1f97b8a33137
出典データセット
uspto-grants-2009_02
特許番号
US07491716B2

反応ノート

読み込み中…