Hydrochloric Acid → 3-(4-{[(2-Methyl-1,3-thiazol-4-yl)carbonyl]amino}-1H-indazol-6-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (80 mg, 0.237 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (71 mg, 0.285 mmol), Pd(dppf)Cl2 (19 mg, 0.024 mmol) and 2 M sodium carbonate (aq) (0.356 ml, 0.712 mmol) were combined in 1,4-dioxane (1 ml) and water (1 ml). The reaction was heated in a Biotage microwave at 150° C. for 15 mins. The pH was adjusted to ˜2 with 2 M HCl (aq) and the solid formed was separated. The solid was extracted with 80% DCM in MeOH (3×25 ml) and the combined organic solvent was evaporated. The residue was dissolved in MeOH:DMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B). The solvent of product-containing fractions was dried under a stream of nitrogen.

Provenance & Evidence