Morpholine → 4-(5-Bromo-1,3-thiazol-2-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

A solution of 2,5-dibromothiazole (0.500 g, 2.06 mmol) in DIPEA (1.50 mL) was charged with morpholine (0.179 mL, 2.06 mmol) and heated to 110° C. for 2 h. The reaction mixture was allowed to cool then partitioned between EtOAc and H2O, and the layers were separated. The aqueous layer was re-extracted with EtOAc (3×), and the combined organic extracts were washed with brine (2×), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica gel [eluting with 5% EtOAc in CHCl3] resulting in the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ=3.35-3.47 (m, 4H), 3.74-3.86 (m, 4H), 7.09 (s, 1H). MS (ES+): m/z=249.06/251.03 (51/49) [MH+]. HPLC: tR=2.98 min (ZQ2, polar—5 min).

Provenance & Evidence