3,4-Dimethoxyphenylboronic acid → 2-(4-Cyclopropylpiperazin-1-yl)-6-(3,4-dimethoxyphenyl)benzothiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 1.48 mmol) and 3,4-dimethoxyphenylboronic acid (323 mg, 1.78 mmol) in THF—H2O (20 mL, 5:1) was added Pd2(dba)3 (240 mg, 0.148 mmol), followed by P(t-Bu)3BF4 (86 mg, 0.296 mmol) and K3PO4.H2O (1.97 g, 7.4 mmol). The mixture was heated at 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 258 mg (49%) of 2-(4-cyclopropyl-piperazin-1-yl)-6-(3,4-dimethoxybenzo)benzothiazole.

Provenance & Evidence