2-(Chloromethyl)quinoline → 2-((4-(5-(Pyridin-4-yl)oxazol-4-yl)phenoxy)methyl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 4-(5-(pyridin4-yl)oxazol4-yl)phenol (90 mg, 0.38 mmol) in 1 mL of dry DMF was added CsF (115 mg, 0.76 mmol). After stirring for 0.5 h, 2-(chloromethyl)quinoline (67 mg, 0.38 mmol) was added and the reaction was heated at 80° C. for 48 h. Upon removal of DMF under vacuum, the residue was purified by PTLC (1:2 hexane/EtOAc) to give 29 mg (20%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ: 5.47 (s, 2H), 7.11 (m, 2H), 7.56 (m, 5H), 7.70 (d, 1H), 7.78 (t, 1H), 7.86 (d, 1H), 8.01 (s, 1H), 8.12 (d, 1H), 8.26 (d, 1H), 8.57 (d, (2H). MS m/z: 380 [M+1]+.

Provenance & Evidence