3-(Bromomethyl)-5-chloro-1-benzothiophene → 3-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one

HRID 215976ノート

反応式

HRID 215976 の反応式
Br.[N:2]1[C:3](=[O:11])[CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.Br[CH2:13][C:14]1[C:15]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1>C1COCC1>[Cl:23][C:21]1[CH:20]=[CH:19][C:16]2[S:17][CH:18]=[C:14]([CH2:13][CH:4]3[N:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]4=[N:2][C:3]3=[O:11])[C:15]=2[CH:22]=1

参加物

4

反応物 2

HCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 44121307Imidazo[1,2-a]pyridin-2(3H)-one hydrobromide

生成物 1

HCID 591767543-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound.

後処理

  1. customthe mixture is quenched with saturated ammonium chloride solution
  2. extractionThe product is extracted with ethyl acetate
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography

出典と根拠

ORDレコード
ord-cf3469b4829544b29c2a2d2397c5ce5f
出典データセット
uspto-grants-2012_06
特許番号
US08193214B2

反応ノート

読み込み中…