1,4-Dioxane → N-1H,1'H-4,6'-Biindazol-4'-yl-2-methyl-1,3-thiazole-4-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]-2-methyl-1,3-thiazole-4-carboxamide (50 mg), Solvias catalyst (7 mg), tripotassium phosphate (101 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (available from J&W Pharmlab, 29 mg), 1,4-dioxane (0.5 ml) and water (0.1 ml). The reaction was heated under microwave irradiation for a total of 60 min at 80° C., then 30 min at 120° C. The reaction was passed through a silica cartridge preconditioned with methanol, washing with methanol, then dried in vacuo. The residue was subjected to a DCM/water wash, dried through a hydrophobic frit and dried in vacuo. The residue was dissolved in DMSO:methanol (1 ml, 1:1, v/v) and purified by MDAP (Method D). Appropriate fractions were evaporated under a stream of nitrogen. The residue was dissolved in methanol and a few drops of 2M HCl (aq) were added and the reaction was stirred for 30 min. The reaction was diluted with methanol and passed through an aminopropyl cartridge, pre-conditioned with methanol, washing with methanol, then dried to give title compound, 11 mg.

Provenance & Evidence