Sodium Carbonate → 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

3-Bromo-5-nitro-1-trityl-1H-indazole (1 g, 0.002 mol) was added to a vial containing pyridin-4-ylboronic acid (0.279 g, 0.00227 mol) and tetrakis(triphenylphosphine)-palladium (0.1155 g, 0.0001 mol). After purging the vial with nitrogen gas, dioxane (6 L) and 2M sodium carbonate (0.006 mol) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for 16 h. Upon completion, the mixture was concentrated under vacuo. Water (3 mL) was added and was extracted using dichloromethane (3×3 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using flash chromatography (1:1 Hexane:Ethyl Acetate). Pure product (0.8954 g, 92.8% yield) was recovered.

Provenance & Evidence