Sodium Iodide → 3-Carboethoxy-8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1386091노트

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HRID 1386091 반응식
[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2].[CH3:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([CH3:27])[C:19]=1[CH2:20]Br.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:20][C:19]3[C:18]([CH3:17])=[CH:25][C:24]([F:26])=[CH:23][C:22]=3[CH3:27])[C:9]2=[N:8][C:7]=1[CH3:16])([O:3][CH2:4][CH3:5])=[O:2]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylateHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

생성물 1

HCID 217173463-Carboethoxy-8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine수율 83%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-carboethoxy-8-hydroxy-2-methylimidazo[1,2-a]pyridine (1.5 g, 6.8 mmol), 2,6-dimethyl-4-fluorobenzylbromide (1.6 g, 7.5 mmol), sodium iodide (0.1 g), potassium carbonate (1.9 g, 13.6 mmol) and acetonitrile (50 ml) was refluxed for over night. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with water, dried over Na2SO4 and evaporated. The residue was chromatographed on silica, eluting with heptane:isopropyl ether(1:2) to give 2.0 g (83%) of the desired product.

후처리

  1. temperaturewas refluxed for over night
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with heptane:isopropyl ether(1:2)

출처 및 근거

ORD 기록
ord-7f5adcc52cc344599489a4a9a2a1bda9
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265415B1

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