Potassium Iodide → Methyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

HRID 2184303ノート

反応式

HRID 2184303 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[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>[CH3:15][C:13]1[N:14]=[C:3]2[C:2]([NH:1][CH2:20][C:19]3[C:22]([CH3:26])=[CH:23][CH:24]=[CH:25][C:18]=3[CH3:17])=[CH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]2[C:12]=1[CH3:16]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

生成物 1

HCID 12148917Methyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate収率 19%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.8 g, 3.6 mmol), 2,6-dimethylbenzylchloride (0.57 g, 3.7 mmol), sodium carbonate (1.0 g, 9.4 mmol) and a catalytic amount of potassium iodide were added to acetonitrile (10 ml) and were refluxed for 20 h. Following filtration, the salts were washed with methylene chloride and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride: ethyl acetate (75:25) as eluent. The yellow residue was treated with hexane to give 0.23 g (19%) of the title product.

後処理

  1. temperaturewere refluxed for 20 h
  2. filtrationfiltration
  3. washthe salts were washed with methylene chloride
  4. customthe solvents were evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. additionThe yellow residue was treated with hexane

出典と根拠

ORDレコード
ord-8070a1fda11944f288fdfa064471510c
出典データセット
uspto-grants-2005_05
特許番号
US06900324B2

反応ノート

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