3-Pyridinylboronic acid → HCID 86629521, compound

Participants

Reaction Conditions

Reaction Steps

To an argon-degassed solution of 6-chloro-2,4-dimethyl-N—((R)-3-{4-[(thiophen-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-nicotinamide (100 mg, 0.23 mmol) and 3-pyridine boronic acid (56 mg, 0.46 mmol) in DME/2 M Na2CO3 (5:2, 3.5 ml) was added Pd(PPh3)4 (15 mg, 0.013 mmol) and the reaction stirred at 90° C. overnight. The mixture was cooled, diluted with CH2Cl2 (25 ml) and saturated aqueous NaHCO3 (25 ml). The aqueous layer was extracted with CH2Cl2 (2×10 ml) and the combined organic extracts were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (CH2Cl2MeOH/NH4OH, 96:4:0 then 88:10:2) to afford 4,6-dimethyl-[2,3′]bipyridinyl-5-carboxylic acid ((R)-3-{4-[(thiophen-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-amide as a mixture of product and starting amine (˜25%).

Provenance & Evidence