Ethyl Acetate → HCID 117653246, compound

Participants

Reaction Steps

To a solution of 5-bromo-4-(4-cyano-3-fluorophenoxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 1, 220 mg, 0.35 mmol) in THF (8 mL), AcOH (10 mL) and water (2.5 mL) was added zinc dust (800 mg, 12.2 mmol). The reaction mixture was left to stir at room temperature for 70 hours. To the reaction mixture was added EtOAc (25 mL) and the mixture filtered through celite and washed with EtOAc (50 mL). The filtrate was retained and to this was added saturated aqueous NaHCO3 (80 mL). The organic layer was retained, dried over MgSO4, and the solvent removed in vacuo. The residue was purified using reverse phase column chromatography eluting with acetonitrile and water (acidic). The residue was dissolved in DCM and treated with TFA (0.3 mL) and stirred at room temperature for 1 hour. The reaction was concentrated in vacuo azeotroping with MeOH. The residue was purified using preparative HPLC to afford the title compound as a colourless powder (16 mg, 26%).

Provenance & Evidence