Phenacyl bromide → 3-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357026ノート

反応式

HRID 357026 の反応式
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][S:15][C:14]2=[O:19])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O>C(O)C>[C:24]1([C:22]2[N:1]=[C:2]3[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]4[C:17](=[O:18])[CH2:16][S:15][C:14]4=[O:19])=[CH:6][CH:5]=[CH:4][N:3]3[CH:21]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 6259Phenacyl bromideHCID 189367033-[4-(2-Aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione

生成物 1

HCID 189368343-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 5.69 g (20 mmol) of 3-[4-(2-aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione in 40 ml of ethanol, 3.98 g (20 mmol) of bromoacetophenone was added at room temperature, followed by refluxing for 1.5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4) to yield 5.24 g (68.7%, light orange crystal) of the desired product.

後処理

  1. temperatureby refluxing for 1.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4)

出典と根拠

ORDレコード
ord-1c189bca81e24e9a9ce5011aed1bb25c
出典データセット
uspto-grants-1998_11
特許番号
US05840732

反応ノート

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