Chlorosuccinimide → 3-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine

HRID 619538ノート

反応式

HRID 619538 の反応式
[C:1]([C:6]1[N:10]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[Cl:16]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:1]([C:6]1[N:10]2[C:11]([CH2:15][Cl:16])=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

参加物

6

反応物 3

HCID 31398ChlorosuccinimideHCID 11816548Ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 86754554Trifluoroacetic acid ethyl acetate

生成物 1

HCID 108575483-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine収率 71.2%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution prepared by dissolving 430 mg (2.06 mM) of 3-carbethoxy-5-methylimidazo[1,2-a]pyridine in 10 ml of ethyl acetate was added 330 mg (2.67 mM) of N-chlorosuccinimide. Then, 1.03 ml (1.03 mM) of 1N-tri-fluoroacetic acid-ethyl acetate was added dropwise at room temperature. The mixture was stirred under argon gas at room temperature for 14 hours. After the reaction, the reaction mixture was poured in 30 ml of saturated aqueous NaHCO3 solution with ice-cooling and the mixture was extracted with 20 ml of ethyl acetate. The organic layer was washed with 30 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to provide 350 mg (yield 71.2%) of the title compound as yellow liquid.

後処理

  1. customTo a solution prepared
  2. customAfter the reaction
  3. temperaturecooling
  4. extractionthe mixture was extracted with 20 ml of ethyl acetate
  5. washThe organic layer was washed with 30 ml of saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

出典と根拠

ORDレコード
ord-baab5c16d39643caa6589dfdaa542212
出典データセット
uspto-grants-1999_09
特許番号
US05958942

反応ノート

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