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

HRID 427500노트

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HRID 427500 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.[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21]Cl)[CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(Cl)Cl.C(#N)C>[CH3:15][C:13]1[N:14]=[C:3]2[C:2]([NH:1][CH2:21][C:20]3[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:17][CH3:18])=[CH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:4]2[C:12]=1[CH3:16]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateHCID 121489182-Ethyl-6-methylbenzyl chloride

생성물 1

HCID 18357442Methyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate수율 38%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.7 g, 3.2 mmol), 2-ethyl-6-methylbenzylchloride (0.54 g, 3.2 mmol), potassium carbonate (0.9 g, 6.4 mmol) and a cat. amount of potassium iodide were added to acetonitrile (20 ml) and were refluxed for 6 h. Following filtration, the acetonitrile was evaporated under reduced pressure to give an oil. The oily residue was solved in methylene chloride and washed with water. The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure to give a solid. Purification by column chromatography on silica gel using methylene chloride:ethylacetate (10:1) as eluent gave 0.42 g (38%) of the title compound.

후처리

  1. temperaturewere refluxed for 6 h
  2. filtrationfiltration
  3. customthe acetonitrile was evaporated under reduced pressure
  4. customto give an oil
  5. washwashed with water
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. customevaporated under reduced pressure
  9. customto give a solid
  10. customPurification by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-13c20cc0099640b8a5ffee934be0148a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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