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

HRID 1170381ノート

反応式

HRID 1170381 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 22004815Ethyl acetate n-butanol溶媒

反応条件

温度
23 °C

実験手順

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/CI) 379.4 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-ce4ca6a30ed2475fb523a4c7a2302a04
出典データセット
uspto-grants-2010_11
特許番号
US07825254B2

反応ノート

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