Ethanol → 2-((3-(Dimethylamino)propyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-6-((3-(dimethylamino)propyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 165.1, 88 mg, 0.185 mmol), pyridin-3-ylboronic acid (22.7 mg, 0.185 mmol) and Na2CO3 (59 mg, 0.555 mmol) in a mixture of DME (4.0 mL), EtOH (0.54 mL) and water (0.80 mL) was flushed with argon for 5 min. Pd(PPh3)2Cl2 was added (6.5 mg, 0.0093 mmol) and the mixture was subjected to MW irradiation at 125° C. (MW irradiation) for 30 min. Additional pyridin-3-ylboronic acid (22.7 mg, 0.185 mmol), Na2CO3 (59 mg, 0.555 mmol) and Pd(PPh3)2Cl2 (6.5 mg, 0.0093 mmol) were added and the mixture stirred at 125° C. for further 30 min. The vial was cooled to RT and the RM was evaporated to dryness under reduced pressure to give a residue that was triturated with THF and filtered. The filtrate was evaporated to dryness under reduced pressure and the crude product was purified by preparative LC-MS. TFA was removed using a SPE PL-HCO3 (StratoSpheres™ VariPure IPE) cartridge to afford the title compound. LC-MS (Condition 6) tR=1.33 min, m/z=474.0 [M+H]+.

Provenance & Evidence