Sodium Carbonate → N-[6-(6-cyano-1H-indol-4-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

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2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.104 mmol), 4-bromo-1H-indole-6-carbonitrile (252 mg, 0.114 mmol), Pd(dppf)Cl2 (8 mg, 0.01 mmol) and sodium carbonate (44 mg, 0.415 mmol) were added to a 0.5-2 ml microwave vial and suspended in 1,4-dioxane (0.5 mL) and water (0.5 mL). The mixture was heated in the microwave at 140° C. for 20 min, then cooled and passed through a 1 g silica cartridge which was washed with methanol. The solvent was evaporated by blow down. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v) and purified by Mass Directed Auto Preparative HPLC (Method F). To the sample-containing fractions 2M HCl (aq) (ca. 1 ml) was added and the fractions were blown down. The residue was dissolved in DCM:methanol (ca. 50:50, v/v) and passed through a 1 g PS—NH2 cartridge, washing with DCM:methanol. Solvent was removed by blow down then the residue was suspended in 2 ml dioxane:water (1:1, v/v) and freeze dried to afford the title compound as a white solid (22 mg).

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