Cesium carbonate → 2-((4-(5-(pyridin-4-yl)-1H-imidazol-1-yl)phenoxy)methyl)quinoline

HRID 33942노트

반응식

HRID 33942 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]=[N:9][CH:8]=2)=[CH:3][CH:2]=1.Cl.Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C.C(O)CCC>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:21][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)=[CH:14][CH:13]=3)[CH:10]=[N:9][CH:8]=2)=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 597975064-(5-(pyridin-4-yl)-1H-imidazol-1-yl)phenol

생성물 1

HCID 117106112-((4-(5-(pyridin-4-yl)-1H-imidazol-1-yl)phenoxy)methyl)quinoline수율 99%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 22004815Ethyl acetate n-butanol용매

반응 조건

온도
23 °C

실험 절차

A mixture of Preparation 84 (4-(5-(pyridin-4-yl)-1H-imidazol-1-yl)phenol, 95 mg, 0.4 mmol), 2-chloromethylquinoline hydrochloride (128 mg, 0.6 mmol), and cesium carbonate (391 mg, 1.2 mmol) in dimethylsulfoxide (2 mL) was stirred at 23° C. for 24 h. The mixture was diluted with ethyl acetate/n-butanol (100 mL/5 mL), was washed with water and then brine, and the organic layer was dried (MgSO4), was filtered, and was concentrated in vacuo. The residue was purified by silica gel chromatography using chloroform/methanol (50:1) to afford 150 mg (99% yield) of the title compound; diagnostic 13C NMR signals (100 MHz, CDCl3) δ 158.940, 157.116, 149.990, 147.836, 141.054, 137.405, 130.989, 130.204, 129.650, 129.239, 127.953, 127.871, 127.392, 127.011, 121.627, 119.324, 116.198, 71.990; MS (AP/Cl) 379.4 (M+H)+.

후처리

  1. washwas washed with water
  2. dry with materialbrine, and the organic layer was dried (MgSO4)
  3. filtrationwas filtered
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-d70d16fa956848ad8bd4d3f810983b07
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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