Dimethylformamide → 2-[[2-(dimethylcarbamoylamino)pyridin-4-yl]methylamino]-N-(2-methylindazol-6-yl)benzamide

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2-[(2-Bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide (110 mg, 0.25 mmol, prepared as detailed infra in Example 4A) and 1,1-dimethylurea (114 mg, 1.3 mmol) were suspended in dioxane (3 mL) under a nitrogen atmosphere and treated consecutively with DMF (1 mL), cesium carbonate (98 mg, 0.3 mmol), Pd2 dba3 (5 mg, 0.005 mmol) and Xantphos (9 mg, 0.015 mmol). The reaction mixture was flushed with nitrogen and heated for 5 hours at 110° C. (bath temperature). On cooling the reaction was concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The organic phase was washed with brine, dried, filtered and concentrated in vacuo. The residue was purified by chromatography on Isolute® flash silica get (Separtis) (Gradient elution: 100% CH2Cl2 to CH2Cl2/EtOH 95:5) to give 2-{[2-(3,3-dimethyl-ureido)-pyridin-4-ylmethyl]-amino}-N-(2-methyl-2H-indazol-6-yl)-benzamide (79 mg, 71%) as a solid; 1 H-NMR (300 MHz, d6-DMSO) 10.15 (1H, s), 8.80 (1H, s), 8.25 (1H, s), 8.13 (1H, d), 8.10 (1H, s), 7.95 (1H, t), 7.82 (1H, s), 7.72 (1H, d), 7.63 (1H, d), 7.22-7.32 (2H, m), 6.95 (1H, d), 6.68 (1H, t), 6.54 (1H, d), 4.45 (2H, d), 4.13 (3H, s), 2.91 (6H, s); m/z (ES+) 444 [M+H]+, 223; Mp. 184° C.

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