Chloroacetaldehyde → Ethyl imidazo[1,2-a]pyridine-8-carboxylate

HRID 1046526노트

반응식

HRID 1046526 반응식
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH2:11])[CH3:2].Cl[CH2:14][CH:15]=O.C([O-])(O)=O.[Na+]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[N:7]([CH:14]=[CH:15][N:11]=2)[CH:8]=[CH:9][CH:10]=1)=[O:12])[CH3:2]

참가 물질

5

반응물 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 12433260Ethyl 2-aminopyridine-3-carboxylate

생성물 1

HCID 10867135Ethyl imidazo[1,2-a]pyridine-8-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-nicotinic acid ethyl ester (13.845 g), ClCH2CHO (58 mL), and NaHCO3 (11.85 g) was stirred in EtOH (500 mL) at reflux overnight. The reaction mixture was concentrated, diluted with H2O, and extracted with DCM. The product was purified by ISCO using 100% EtOAc first (to remove unreacted starting material), then using 100% DCM to 5% MeOH/DCM. The product eluted at 3% MeOH/DCM, providing imidazo[1,2-a]pyridine-8-carboxylic acid ethyl ester (10.5 g).

후처리

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with H2O
  4. extractionextracted with DCM
  5. customThe product was purified by ISCO
  6. custom100% EtOAc first (to remove unreacted starting material)
  7. washThe product eluted at 3% MeOH/DCM

출처 및 근거

ORD 기록
ord-f1c525b73ae34ebfb03b5afdde225f3e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569306B2

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