Sulfuric Acid → Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

HRID 1045408노트

반응식

HRID 1045408 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[K].Cl[C:11](=[CH:17]O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][N:8]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 706222-Amino-5-bromopyridineHCID 86677443Ethyl 2-chloro-3-hydroxyacrylate potassium salt

생성물 1

HCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
78 °C

실험 절차

To a stirring suspension of 5-bromopyridin-2-amine (1.2 g, 7.05 mmol) and ethyl 2-chloro-3-hydroxyacrylate potassium salt (6.6 g, 28.19 mmol) (prepared in a similar manner as 22) in EtOH (100 mL) at room temperature was added sulfuric acid (751 μL, 14.10 mmol) dropwise. The reaction mixture was heated at 78° C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the pH was adjusted between 6-8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic was washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography to yield ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (24s). MS m/z 270.2 (M+1)+.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationthe solvent was concentrated
  3. extractionThe crude product was extracted with ethyl acetate
  4. washThe organic was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe crude product was purified by silica chromatography

출처 및 근거

ORD 기록
ord-85b1635426cf432a93361adf2b5213e2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569283B2

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