Sodium Carbonate → 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A reaction vessel was charged with N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2 sulfonamide (Intermediate E) (4 g, 7.05 mmol), 2-bromo-1-iodo-4-(trifluoromethyl)benzene (4.95 g, 14.10 mmol) and Pd(dppf)Cl2 DCM (1.151 g, 1.410 mmol). Dioxane (35.2 mL) and t-butanol (35.2 mL) were added to the reaction mixture followed by sodium carbonate in water (1.9 M) (11.13 mL, 21.15 mmol). The reaction vial was then swept with nitrogen and sealed with a screw cap. The resulting mixture was then heated to 50° C. and stirred for 4 hours. LC/MS indicated that the product was formed. The resulting mixture was transferred to a separatory funnel containing water and the aqueous layer was washed three times with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated to a dark oil which was purified by MPLC using 120 g silica gel column eluting with 0 to 70% EtOAc in heptane) to afford 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (3.27 g, 4.92 mmol) as a white solid. m/z (ESI) 685.8 [M+Na]+.

Provenance & Evidence