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

HRID 910079노트

반응식

HRID 910079 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffe5fdf77c914f9bb173af50fbc0eaee
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022065B2

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