Potassium Carbonate → HCID 21914168, compound

Participants

Reaction Conditions

Reaction Steps

In a 3-neck 500 mL round bottomed flask equipped with a stir bar, condenser and nitrogen lines was placed was placed 2-iodo-1-methoxy-4-nitrobenzene (7.0 g, 25.1 mmol), 3-chlorophenylboronic acid (4.32 g, 27.6 mmol), potassium carbonate (10.4 g, 75.3 mmol), triphenylphosphine (1.98 g, 7.53 mmol), 1,4-dioxane (50 mL), 50% aqueous EtOH followed by palladium acetate (564 mg, 2.51 mmol). The mixture was heated to 90° C. in an oil bath for 16 hours and then quenched with 1M aqueous HCl (80 mL). After the reaction mixture was filtered through Celite, water (100 mL) and 1M aqueous HCl (100 mL) were added followed by extractions with ethyl acetate (3×150 mL). The organic portions were combined, washed with brine (250 mL), dried (MgSO4) and concentrated. The residue was purified by column utilizing 20% EtOAc/Hexanes as the eluent to produce 4.26 g of I-256 as an orange solid in 64% yield. MS (ESI+): 263.3 (M+).

Provenance & Evidence