Sulfuric Acid → Ethyl 8-bromo-6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

HRID 931041

반응식

HRID 931041 반응식
[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][O-].[K+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[Br:10][C:9]1[C:2]2[N:3]([C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:1]=2)[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 14912506-Amino-5-bromopyridine-3-carbonitrileHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

생성물 1

HCID 118378872Ethyl 8-bromo-6-cyanoimidazo[1,2-a]pyridine-3-carboxylate수율 46%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 6-amino-5-bromonicotinonitrile (6.3 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (15 g), sulfuric acid (2.2 mL) and ethanol (160 mL) was heated with reflux for 30 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.3 g).

후처리

  1. temperaturewas heated
  2. temperaturewith reflux for 30 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2a2c8c3ab2aa495b82ba7df419346a5a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296746B2

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