Acetone → N-{4-[3-(4-{2-[Methyl-(1-methyl-1H-pyrazole-4-sulfonyl)-amino]-ethyl}-piperazin-1-yl)-pyridin-2-yl]-phenyl}-acetamide dihydrochloride

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide (230 mg, 0.58 mmol) in DMA-H2O (6 mL; 5:1 v/v, previously degassed with nitrogen). Add 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide (181 mg, 0.69 mmol), potassium carbonate (191 mg, 1.38 mmol) and tetrakis(triphenylphosphine)palladium (33 mg, 0.03 mmol). Heat the reaction mixture at 110° C. for 18 hr. Cool and dilute with ethyl acetate and water. Extract the aqueous layer with ethyl acetate and combine the organic layers. Wash the combined organic layers with brine and concentrate. Purify by chromatography, eluting with 1:2 hexanes:acetone to afford the free base of the title compound (228 mg, 79% yield) as a white solid.

Provenance & Evidence