Sodium Bicarbonate → N-Methyl-3-(2-{2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-yl)-benzamide

Participants

Reaction Conditions

Reaction Steps

A microwave tube is charged with [4-(6-bromobenzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine (41 mg, 0.092 mmol), 1.6 equivalent of 3-(methylcarbamoyl)phenylboronic acid (27 mg, 0.15 mmol), 5 mol % of tetrakis(triphenylphosphine)palladium(0) (5.0 mg, 0.0046 mmol), 1.2 equivalent of NaHCO3 (10 mg, 0.11 mmol) and 2:1 DMSO/H2O solution (3 mL). The reaction is sealed and heated under microwave condition at 170° C. for 20 minutes, cooled down, filtered through SCX column and washed several time with dichloromethane/MeOH (1:1). The product is then released with 0.1 M NH3 solution in MeOH, collected and evaporated to give a brown oil. The oil is subjected to reverse phase purification, eluting with 5-95% CH3CN/0.01 N NH4HCO3 in water using a C18 Xterra column, to give the title compound as a pale yellow solid (10 mg, 40% yield). ES+(m/z) 501 [M+H].

Provenance & Evidence