Sodium Hydroxide → HCID 57543436, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (118 mg, 422 μmol), 5-bromo-1-(2-chlorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (130 mg, 384 μmol), Pd(PPh3)4 (0.016 mmol, 19 mg), and sodium carbonate (2 M) (0.576 ml, 1.15 μmol) in 2.0 mL of dioxane in a sealed tube was heated in a microwave at 125° C. for 25 min. The mixture was treated with 2 mL of 1 N NaOH solution, extracted with 2×5 mL of EtOAc. The combined organic phases were washed with 2 mL of brine, dried and concentrated. The brown residue was loaded on an ISCO 12 g column (eluting with a gradient of 1-6% MeOH in DCM) to provide the title compound (140 mg) as an off white crystalline solid. MS (ESI, pos.ion) m/z: 411.2 (M+1).

Provenance & Evidence