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Dimethylformamide → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(2,3-dihydro-1-benzofuran-5-ylmethoxy)pyridin-2 (1H)-one

HRID 2203084
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인쇄 미리보기

반응식

HRID 2203084 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:13]([CH3:19])[C:12]=3[CH:20]=2)[C:4](=[O:21])[CH:3]=1.[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][OH:32])=[CH:30][C:25]=2[CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH:16]1([C:14]2[N:13]([CH3:19])[C:12]3[CH:20]=[C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:32][CH2:31][C:29]5[CH:28]=[CH:27][C:26]6[O:22][CH2:23][CH2:24][C:25]=6[CH:30]=5)=[CH:3][C:4]4=[O:21])[CH:9]=[CH:10][C:11]=3[N:15]=2)[CH2:18][CH2:17]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanolHCID 896909614-Chloro-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

생성물 1

HCID 896912431-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(2,3-dihydro-1-benzofuran-5-ylmethoxy)pyridin-2 (1H)-one수율 29%

시약·촉매·용매

1
HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), (2,3-dihydrobenzofuran-5-yl)methanol (100 mg), cesium carbonate (326 mg) and DMF (3 ml) was heated at 100° C. overnight. The mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (40 mg) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-90cb1a5d736340a9bcd3ce7744f5fb54
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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