4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Participants

Reaction Steps

2-Bromo-6-methoxy-1,3-benzothiazole (49 mg, 0.20 mmol), 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (70 mg, 0.24 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine, with the following exceptions: The reaction was heated for 4 h before the solvent was evaporated under reduced pressure. The residue was dissolved in MeOH/DCM 1:1 and filtered through silica. The filtrate was concentrated and the crude product was purified by preparative HPLC to give the title compound (0.6 mg). 1H NMR (CHLOROFORM-d) δ 8.79 (d, 1 H) 8.18 (dd, 1 H) 7.90 (d, 1 H) 7.35 (d, 1 H) 7.08 (dd, 1 H) 6.71 (d, 1 H) 3.90 (s, 3 H) 3.87-3.83 (m, 4 H) 3.67-3.63 (m, 4 H); MS m/z (M+H) 328.

Provenance & Evidence