Ethanol → 2-((3-Hydroxypropyl)(methyl)amino)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Participants

Reaction Steps

A mixture of 5-bromo-6-((3-hydroxypropyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 165.1, 92 mg, 0.189 mmol), (6-methylpyridin-3-yl)boronic acid (25.9 mg, 0.189 mmol) and Na2CO3 (60 mg, 0.566 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 (6.6 mg, 0.0094 mmol) and the mixture subjected to MW irradiation at 125° C. for 20 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. Additional purification (Isolute Flash Silica gel cartridge, 5 g, elution of impurities with EtOAc, subsequent elution of product with MeOH) afforded the title compound. LC-MS (Condition 5) tR=1.65 min, m/z=461.2 [M+H]+, m/z=459.2 [M−H]−.

Provenance & Evidence