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

HRID 215976노트

반응식

HRID 215976 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf3469b4829544b29c2a2d2397c5ce5f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193214B2

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