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

HRID 1046526ノート

反応式

HRID 1046526 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f1c525b73ae34ebfb03b5afdde225f3e
出典データセット
uspto-grants-2013_10
特許番号
US08569306B2

反応ノート

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