(6-Methoxypyridin-3-yl)boronic acid → 2-(4-Cyclopropylpiperazin-1-yl)-6-(6-methoxypyridin-3-yl)benzothiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (400 mg, 1.18 mmol) and 2-methoxy-5-pyridineboronic acid (217 mg, 1.42 mmol) in THF—H2O (16 mL, 5:1) was added Pd2(dba)3 (191 mg, 0.118 mmol), followed by P(t-Bu)3BF4 (68 mg, 0.236 mmol) and K3PO4.H2O (1.57 g, 5.9 mmol). The mixture was heated to 60° C. for 3 h. The mixture was filtered and the filtrate was evaporated. the residue was diluted with water (5 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated to give the crude product, which was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH (1:50). This afforded 253 mg (58%) of 2-(4-cyclopropyl-piperazin-1-yl)-6-(6-methoxypyridin-3-yl)benzothiazole.

Provenance & Evidence