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

HRID 2184303노트

반응식

HRID 2184303 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8070a1fda11944f288fdfa064471510c
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900324B2

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