Potassium Iodide → Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1166168ノート

反応式

HRID 1166168 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(#N)C>[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:19]=1[CH2:20][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylate

生成物 1

HCID 22672581Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylate収率 56.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Ethyl 8-amino-3-methylimidazo[1,2-a]pyridin-2-carboxylate (4.6 g, 21 mmol), 2,6-dimethylbenzyl chloride (3.2 g, 21 mmol), sodium carbonate (4.4 g, 42 mmol) and a cat amount of potassium iodide were added to acetonitrile (50 ml) and refluxed for 3 h., stirred for 20 h. at room temperature and refluxed for 1 h. The solids were removed by filtration and the solvents were evaporated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent and crystallization from ethyl acetate gave 4.0 g (56%) of the desired product.

後処理

  1. temperaturerefluxed for 3 h.
  2. temperaturerefluxed for 1 h
  3. customThe solids were removed by filtration
  4. customthe solvents were evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure
  10. customPurification of the residue by column chromatography on silica gel
  11. customcrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-39587510fa604c43ba0d650a283b19d8
出典データセット
uspto-grants-2003_09
特許番号
US06613775B1

反応ノート

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