Ethyl chloroformate → Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate

HRID 1429919ノート

反応式

HRID 1429919 の反応式
C([Li])CCC.[Cl:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1.[C:16](Cl)(=[O:20])[O:17][CH2:18][CH3:19]>C1COCC1>[Cl:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[C:16]([O:17][CH2:18][CH3:19])=[O:20]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 21139722-Chloroimidazo[1,2-a]pyridineHCID 178418339Butyllithium

生成物 1

HCID 21643308Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate収率 89.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-Butyllithium (1.6M in hexane, 45.1 mL) was added to a solution of 2-chloroimidazo[1,2-a]pyridine (10 g) in THF (120 mL) at −78° C. After stirring for 30 min, ethyl chlorocarbonate (7.82 g) in THF (10 mL) was added to the mixture at the same temperature and stirred for 1 h and then 10 h at room temperature. The mixture was quenched with water, and extracted with ethyl acetate, and the extract was washed with brine, and dried over magnesium sulfate. The residue was purified by column chromatography (silica gel, eluted with 10%-50% EtOAc in hexane) to give ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (13.20 g) as an off-white solid.

後処理

  1. stirringstirred for 1 h
  2. custom10 h
  3. customat room temperature
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. washthe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe residue was purified by column chromatography (silica gel, eluted with 10%-50% EtOAc in hexane)

出典と根拠

ORDレコード
ord-5a893128e35a4e5086f7a1b6f4a34f9b
出典データセット
uspto-grants-2015_01
特許番号
US08940758B2

反応ノート

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