Sodium Bicarbonate → 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

HRID 2372183노트

반응식

HRID 2372183 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](C(Br)C)[N:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[CH:11]([CH3:12])[O:10][C:8](=[O:9])[C:7]=12

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 19902854Ethyl 4-chloro-2-(1-bromoethyl)nicotinate

생성물 1

HCID 199028524-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A mixture of ethyl 4-chloro-2-(1-bromoethyl)nicotinate (7.45 g) and sodium bicarbonate (4.00 g) in 50 ml of DMSO is heated at 120°, under nitrogen, for 2 hours, after which it is cooled, diluted with water, filtered and extracted with ether. The combined organic layers are washed with water and concentrated. The residue is taken into ethyl acetate, washed with brine, dried, concentrated and purified by flash chromatography to give 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one, which is then reacted with N-bromosuccinimide and 2,2'-azobis(2-methylpropionitrile), as above, to give 7-bromo-4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one.

후처리

  1. temperatureis heated at 120°, under nitrogen, for 2 hours
  2. temperatureafter which it is cooled
  3. filtrationfiltered
  4. extractionextracted with ether
  5. washThe combined organic layers are washed with water
  6. concentrationconcentrated
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated
  10. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-577f714f52a74b5ebae5ea0ca3fb61ad
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05098462

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