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Sodium hydride → 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

HRID 2203112
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인쇄 미리보기

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HRID 2203112 반응식
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[H-].[Na+].Br[C:12]1[CH:17]=[CH:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]3[N:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[N:23]([CH3:29])[C:22]=3[CH:30]=2)[C:14](=[O:31])[CH:13]=1>CC(N(C)C)=O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:12]2[CH:17]=[CH:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([CH:26]5[CH2:28][CH2:27]5)[N:23]([CH3:29])[C:22]=4[CH:30]=3)[C:14](=[O:31])[CH:13]=2)[N:6]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2763211(2-Bromo-1,3-thiazol-4-yl)methanolHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

생성물 1

HCID 1213862714-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
0 °C

실험 절차

To a solution of (2-bromo-1,3-thiazol-4-yl)methanol (169 mg) in DMA (5 ml) was added NaH (60% in oil, 34.9 mg) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one was added to the reaction mixture, and the mixture was stirred at 120° C. under N2 atmosphere for 30 min. The reaction mixture was quenched with water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (57.0 mg) as a white solid.

후처리

  1. stirringthe mixture was stirred at 120° C. under N2 atmosphere for 30 min
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by NH silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-2b83714397b64e35bde56e73cdb92fb5
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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