Aniline → HCID 57484939, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL microwave vial were sequentially added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.100 g, 0.267 mmol), cesium carbonate (0.305 g, 0.936 mmol), 1,4-Dioxane (2.5 mL) and aniline (0.049 mL, 0.535 mmol). The stirring suspension was degassed with nitrogen for 10 min. Added next were BINAP (0.033 g, 0.053 mmol) and palladium(II) acetate (6.01 mg, 0.027 mmol). The sealed mixture was stirred at 105° C. overnight. After cooling to room temperature, the contents were poured onto EtOAc and filtered through Celite. The filter pad was washed with additional 50% THF/EtOAc. The combined filtrates were treated with silica gel and concentrated in vacuo. The crude product was purified by silica gel chromatography (dry loaded, eluent: Gradient 5-80% of DCM and chloroform containing 10% 2M Ammonia (in methanol))). The isolated solid was dried in a vacuum oven overnight and the final product collected as 0.061 g (52%). LCMS E-S (M+H)=431.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, J=6.57 Hz, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 4.35 (d, J=5.05 Hz, 2H), 4.98-5.11 (m, 1H), 5.90 (s, 1H), 6.93-7.00 (m, 2H), 7.34 (t, J=7.96 Hz, 2H), 7.86 (d, J=7.58 Hz, 2H), 7.97 (s, 1H), 8.59 (t, J=5.05 Hz, 1H), 9.62 (s, 1H), 11.58 (br. s., 1H).

Provenance & Evidence