Nitrogen → HCID 57863450, compound

Participants

Reaction Steps

In a stirred septum capped vial, charge 2-(4-bromo-2-fluoro-phenyl)-N-(4-tert-butyl-pyridin-2-yl)-acetamide (400 mg, 1.09 mmol), 7-(6-methyl-pyridin-2-yl)-imidazo[1,2-a]pyridine (228 mg, 1.09 mmol), KOAc (213 mg, 2.18 mmol), PdCl2(PPh3)2 and flushes with N2 needle for 15 minutes then one adds DMSO (5 mL) and de-oxygenate with N2 needle and places vial in oil bath at 80 to 90° C. for 24 hours. Cool the reaction then purify by passing through Varian SCX® (10 g) column that is pre-washed with water and methanol, the product being eluted with (20%) 2 N NH3 in methanol/(80%) DCM. Evaporate solvent from the product containing fractions under reduced pressure. Chromatograph using (40 g ISCO®) SiO2 eluting with a gradient of 0% to 10% 2 M NH3 in MeOH with the balance DCM. Evaporate solvents and purify by reverse phase chromatography (C-18 acetonitrile/H2O with 0.1% TFA) Neutralize, extract, and strip off solvents. Dry in vacuum oven to afford 118.4 mg (21.9%) MS(ES), m/z 494 (M+1).

Provenance & Evidence