Sodium Bicarbonate → 7-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridine

HRID 895451

반응식

HRID 895451 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13](=O)[CH2:14]Br.C([O-])(O)=O.[Na+]>C(O)C>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:14]=[C:13]([C:12]3[CH:17]=[CH:18][C:19]([CH3:20])=[C:10]([CH3:9])[CH:11]=3)[N:1]=[C:2]2[CH:7]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5818662-Amino-4-chloropyridineHCID 37031132-Bromo-1-(3,4-dimethylphenyl)ethan-1-one

생성물 1

HCID 98815617-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridine수율 69.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 2-amino-4-chloro-pyridine (0.39 g, 3.03 mmol) in ethanol (25 ml) was added 3,4-dimethyl-phenacylbromide (0.69 g, 3.03 mmol). The reaction mixture was stirred under reflux conditions for 16 h, poured into sat. NaHCO3 solution (70 ml) and extracted with dichloromethane (70 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give the crude product as a brown solid (0.84 g). Further purification by column chromatography on silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane yielded the title compound (0.54 g, 69%) as a pale yellow solid, m.p. 144° C. and MS: m/e=256.2 (M+).

후처리

  1. extractionextracted with dichloromethane (70 ml)
  2. washThe combined organic layers were washed with brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give the crude product as a brown solid (0.84 g)
  6. customFurther purification by column chromatography
  7. customon silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-d221bb7c370d4e2f9463d509bd653e39
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916826B2

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