Propargyl bromide → 5-(4-Chloro-phenyl)-2-prop-2-ynyloxy-pyridine

Reaktionsgleichung

Br[CH2:2][C:3]#[CH:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[N:16][CH:17]=2)=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:4][C:3]#[CH:2])=[N:16][CH:17]=2)=[CH:8][CH:7]=1

Komponenten

Versuchsvorschrift

2 mL (80% in toluene, 18.5 mmol) 3-bromo-propyne are added to a suspension of 3.8 g (18.5 mmol) 5-(4-chloro-phenyl)-pyridin-2-ol and 5.1 g (37 mmol) K2CO3 in 50 mL DMF and the reaction mixture is stirred for 64 h at RT. The mixture is evaporated down i. vac., the residue is combined with 80 mL water, extracted with 150 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 2:1).