Ethanol → Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

HRID 79240

반응식

HRID 79240 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C(O)C.Cl[CH:13]([CH:19]=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][N:8]=[C:4]2[CH:3]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 6932822-Amino-4-bromopyridine

생성물 1

HCID 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
60 °C

실험 절차

4-Bromopyridin-2-amine (10.0 g, 0.06 mol) was mixed with ethanol (50 mL) in a reaction flask, under an atmosphere of dry nitrogen. A solution of ethyl 2-chloro-3-oxopropanoate (5% in benzene; 222 mL; Commercial solution from Toronto Research Chemicals Inc.) was added. The mixture was heated to 60° C. under nitrogen for 5 hours. After allowing the mixture to cool the solvent was removed under vacuum to give a brown solid. The solid was mixed with ethyl acetate (500 mL) and sodium bicarbonate solution (200 mL) and stirred to dissolve. The phases were separated and the bicarbonate solution was extracted further with ethyl acetate (100 mL). The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated under vacuum to give a solid. The crude material was dissolved in ethyl acetate and passed through a short column of silica, eluting with ethyl acetate. Fractions containing the product were concentrated under reduced pressure to give ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (15 g) as a pale yellow solid.

후처리

  1. temperatureto cool the solvent
  2. customwas removed under vacuum
  3. customto give a brown solid
  4. dissolutionto dissolve
  5. customThe phases were separated
  6. extractionthe bicarbonate solution was extracted further with ethyl acetate (100 mL)
  7. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto give a solid
  11. washeluting with ethyl acetate
  12. additionFractions containing the product
  13. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-02283289f9014bd2aa134ceff1d96dd9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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