2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 5-(1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Participants

Reaction Steps

2-Bromo-6-methoxy-1,3-benzothiazole (49 mg, 0.20 mmol) and 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (68 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 stirred for 2 h and was then allowed to reach rt on. The mixture was filtered through a plug of silica and Na2SO4, eluting with DCM. The volume of the filtrate was reduced in a centrifuge and the remainder was purified by HPLC to give the title compound (4.2 mg). 1H NMR (CHLOROFORM-d: CD3OD) δ 8.93 (d, 1 H) 8.21 (dd, 1 H) 7.92 (d, 1 H) 7.68 (d, 1 H) 7.43 (d, 1 H) 7.12 (dd, 1 H) 3.89 (s, 3 H).

Provenance & Evidence