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

HRID 33942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33942
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 22004815Ethyl acetate n-butanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d70d16fa956848ad8bd4d3f810983b07
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429665B2

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