Reaction Steps
N2-(3-Methyl-1-tosyl-1H-indazol-6-yl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine. A mixture of tris(dibenzylideneacetone)dipalladium(0) (0.074 g, 0.081 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.094 g, 0.162 mmol) in 1,4-dioxane (4 mL) was heated briefly with a heat gun until most of the solids had dissolved and then added to 6-bromo-3-methyl-1-tosyl-1H-indazole (0.295 g, 0.809 mmol), N5-((tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-c]pyridine-2,5-diamine (0.200 g, 0.809 mmol), and finely ground cesium carbonate (1.080 g, 3.32 mmol) in a sealable vessel with a stirbar. Nitrogen was blown in to blow out air. The resulting mixture was sealed, stirred vigorously, and heated at 100° C. for 3.5 h. The resulting green mixture was cooled to room temperature. Water (10 mL) was added with vigorous stirring. Solids were collected by vacuum filtration and washed thoroughly with water. The solids were taken up in dimethyl sulfoxide and methanol. The resulting mixture was heated with a heat gun and then quickly filtered. The filtrate was capped and let stand at room temperature for 30 min. Solids were collected by vacuum filtration, washed with methanol and diethyl ether, and dried under high vacuum at 40° C. to give the desired product (0.345 g, 0.649 mmol, 80% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.12 (s, 1H), 8.95 (d, J=1.17 Hz, 1H), 7.78 (d, J=8.20 Hz, 2H), 7.60-7.67 (m, 1H), 7.53-7.60 (m, 1H), 7.49 (t, J=8.20 Hz, 1H), 7.38 (d, J=8.59 Hz, 2H), 6.82 (d, J=8.59 Hz, 1H), 6.20-6.31 (m, 2H), 3.76 (dd, J=3.32, 11.13 Hz, 2H), 3.29 (t, J=6.25 Hz, 2H), 3.18 (t, J=10.93 Hz, 2H), 2.41 (s, 3H), 2.31 (s, 3H), 1.87-2.03 (m, J=4.30, 7.36, 7.36, 7.36, 7.36, 11.16 Hz, 1H), 1.73 (d, J=12.49 Hz, 2H), 1.28 (qd, 2H); MS (ESI) m/z 532.2 [M+1]+.
