2-Bromo-1-(4-hydroxyphenyl)ethanone → 4-(Imidazo[1,2-a]pyridin-2-yl)phenol

HRID 2059513ノート

反応式

HRID 2059513 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])O.[Na+]>C(#N)C>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]3[CH:2]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 104392-AminopyridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 8183334-(Imidazo[1,2-a]pyridin-2-yl)phenol収率 63.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

649 mg (corresponding to 3.0 mmol) of 2-bromo-4′-hydroxyacetophenone and 285 mg (corresponding to 3.0 mmol) of 2-aminopyridine were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110° C. for one hour. After the reaction solution was cooled down to room temperature, 254 mg (corresponding to 5.4 mmol) of sodium hydrogencarbonate was added thereto. The resulting mixture was refluxed in an oil bath at 100° C. for one hour. After the completion of the reaction, the reaction solution was cooled to room temperature, and precipitates were filtered and recovered therefrom. The precipitates were washed with acetonitrile and water, and then dried under reduced pressure to obtain 405 mg (corresponding to 1.9 mmol) of 2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine (FIG. 4, Step 2).

後処理

  1. temperatureAfter the reaction solution was cooled down to room temperature
  2. temperatureThe resulting mixture was refluxed in an oil bath at 100° C. for one hour
  3. customAfter the completion of the reaction
  4. temperaturethe reaction solution was cooled to room temperature
  5. customprecipitates
  6. filtrationwere filtered
  7. customrecovered
  8. washThe precipitates were washed with acetonitrile and water
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-5610be1c99b34922ad05dbfcc85590fa
出典データセット
uspto-grants-2012_10
特許番号
US08277777B2

反応ノート

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