Potassium Carbonate → 6-Bromo-2,3-dimethylimidazo(1,2-a)pyridine

HRID 1943987ノート

反応式

HRID 1943987 の反応式
Br[CH:2]([CH3:6])[C:3](=O)[CH3:4].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([C:2]([CH3:6])=[C:3]([CH3:4])[N:7]=2)[CH:10]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 131422-Butanone, 3-bromo-HCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 145903676-Bromo-2,3-dimethylimidazo(1,2-a)pyridine収率 16.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

13.53 mL (130.06 mmol) of 3-bromobutan-2-one are added to a mixture, stirred at 20° C., of 5 g (28.90 mmol) of 2-amino-5-bromopyridine and 4.85 g (57.80 mmol) of sodium hydrogen carbonate in 100 mL of ethanol. The mixture is refluxed for 12 hours and then concentrated under reduced pressure. The mixture obtained is taken up in 100 mL of water. The pH of the solution is basified by successive additions of potassium carbonate. The mixture is then extracted with 3×50 mL of ethyl acetate. The combined organic phases are washed with water (50 mL), dried over sodium sulfate and then concentrated under reduced pressure. An oil is obtained, which is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol. 1.1 g of the expected product are thus isolated.

後処理

  1. temperatureThe mixture is refluxed for 12 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe mixture obtained
  4. extractionThe mixture is then extracted with 3×50 mL of ethyl acetate
  5. washThe combined organic phases are washed with water (50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customAn oil is obtained
  9. customwhich is purified by chromatography on a column of silica
  10. washeluting with a mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-45ac94157fe94ece9503285807d874bb
出典データセット
uspto-grants-2013_03
特許番号
US08394820B2

反応ノート

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