Sodium Carbonate → 6-nitro-3-(pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 3-iodo-6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (1.2 g, 2.9 mmol, WO 2010/027500, Intermediate 57, Step B), pyridine-4-boronic acid (0.704 g, 5.72 mmol), and Pd(PPh3)4 (0.165 g, 0.143 mmol), 1,4-dioxane (25 mL) and an aqueous solution of Na2CO3 (2 M, 6.3 mL, 12.6 mmol). The vial was sealed and the mixture was heated in a microwave at about 120° C. for about 40 min. The mixture was diluted with EtOAc (100 mL) and water (25 mL) and the layers separated. The aqueous layer was extracted with EtOAc (15 mL). The combined extracts were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography (80 g silica gel) eluting with 20 to 80% EtOAc/heptane to provide 6-nitro-3-(pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (0.893 g, 84%): LC/MS (Table 2, Method c) Rt=3.02 min.; MS m/z: 371 (M+H)+.

Provenance & Evidence