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

HRID 1386091ノート

反応式

HRID 1386091 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7f5adcc52cc344599489a4a9a2a1bda9
出典データセット
uspto-grants-2001_07
特許番号
US06265415B1

反応ノート

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