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

Participants

Reaction Conditions

Reaction Steps

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-2-methyl-1H-indole (22 mg, 0.104 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 DCM:methanol. The solvent was evaporated by blow down. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v), passed through a 1 g C18 cartridge washing with acetonitrile and 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 G). Pure fractions were combined, evaporated to dryness, the residue suspended in 3 ml dioxane:water (1:1, v/v) and freeze dried to afford the title compound as an off-white solid (17 mg).

Provenance & Evidence