Sodium Bicarbonate → 7-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridine

HRID 895451

反応式

HRID 895451 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13](=O)[CH2:14]Br.C([O-])(O)=O.[Na+]>C(O)C>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:14]=[C:13]([C:12]3[CH:17]=[CH:18][C:19]([CH3:20])=[C:10]([CH3:9])[CH:11]=3)[N:1]=[C:2]2[CH:7]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 5818662-Amino-4-chloropyridineHCID 37031132-Bromo-1-(3,4-dimethylphenyl)ethan-1-one

生成物 1

HCID 98815617-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridine収率 69.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of 2-amino-4-chloro-pyridine (0.39 g, 3.03 mmol) in ethanol (25 ml) was added 3,4-dimethyl-phenacylbromide (0.69 g, 3.03 mmol). The reaction mixture was stirred under reflux conditions for 16 h, poured into sat. NaHCO3 solution (70 ml) and extracted with dichloromethane (70 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give the crude product as a brown solid (0.84 g). Further purification by column chromatography on silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane yielded the title compound (0.54 g, 69%) as a pale yellow solid, m.p. 144° C. and MS: m/e=256.2 (M+).

後処理

  1. extractionextracted with dichloromethane (70 ml)
  2. washThe combined organic layers were washed with brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give the crude product as a brown solid (0.84 g)
  6. customFurther purification by column chromatography
  7. customon silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-d221bb7c370d4e2f9463d509bd653e39
出典データセット
uspto-grants-2005_07
特許番号
US06916826B2

関連ノート

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