Dimethylformamide → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrimidin-5-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

7-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.06 g, 0.12 mmol) (Example 127) was dissolved in a 1:1 mixture of dimethoxyethane:dimethylformamide (0.6 mL) in a 2 dram vial. Pyrimidin-5-ylboronic acid (0.02 g, 0.18 mmol), PdCl2(dppf)*dcm (0.005 g, 0.006 mmol), and 2 M sodium carbonate solution (0.17 mL, 0.34 mmol) were added. Nitrogen was bubbled through the reaction mixture for 5 minutes before sealing the vial and heating at 90° C. for 16 hours. The reaction mixture was filtered over a 25 mm nylon filter 0.2 μM. The solids were washed with dimethylformamide (1 mL). The filtrate was concentrated under reduced pressure and dried under high vacuum to give N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrimidin-5-yl)imidazo[1,2-a]pyridine-3-carboxamide (44 mg) as a beige solid. MS (APCI), positive scan, m/z=489.2 (M+H).

Provenance & Evidence