1,4-Dioxane → 1-(1-Methylethyl)-N-[6-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide (70 mg), (2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)boronic acid (29 mg), tripotassium phosphate (103 mg) and Solvias catalyst (9 mg), 1,4-dioxane (1.2 ml) and water (0.24 ml). The reaction was heated under microwave irradiation at 100° C. for 30 min, twice. Further (2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)boronic acid (10 mg) and Solvias catalyst (9 mg) were added and the reaction heated under microwave irradiation at 100° C. for 30 min. Again further (2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)boronic acid (11 mg), tripotassium phosphate (30 mg) and Solvias catalyst (9 mg) were added and the reaction heated under microwave irradiation at 100° C. for 30 min. The reaction was passed through a silica cartridge, preconditioned with methanol, washing with methanol. The solvent was evaporated and the residue was dissolved in DMSO:methanol (1:1, v/v) and purified by MDAP (Method A). Appropriate fractions were evaporated to dryness, dissolved in methanol (2 ml) and 2 M HCl (aq) (0.5 ml) and left at room temperature for 30 min. The solvent was evaporated, the residue was dissolved in DMSO:methanol (1:10, v/v) and passed through an aminopropyl cartridge preconditioned with methanol, washing with methanol. The solvent was evaporated and the residue was purified by MDAP (method A). Purified fractions were evaporated to dryness, dissolved in methanol, passed through an aminopropyl cartridge preconditioned with methanol, washing with methanol, then evaporated to dryness to give title compound, 19 mg.

Provenance & Evidence