Triethylamine → 3-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Steps

A sealable vial was charged with (3-chlorophenyl)boronic acid (25.6 mg, 0.164 mmol), N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (48.9 mg, 0.109 mmol), 3 Å molecular sieves (powdered, 60 mg), DCM (545 μl), and triethylamine (45.6 μl, 0.327 mmol). Copper (II) acetate (39.6 mg, 0.218 mmol) was added as a solid in a single portion. The mixture was stirred at rt for 48 h. The reaction mixture was poured into a mixture of NH4OH and water (10% NH4OH in H2O), extracted with DCM (2×10 mL), organic layers (which were an emulsion) were combined and washed with water (10 mL) then brine (20 mL), the emulsion resolved upon brine wash. The organic layers were dried (Na2SO4) and concentrated for purification by silica gel MPLC. The residue was taken up in minimal DCM and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using 98:2 Heptane:EtOAc to 100% EtOAc gradient to afford 3-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (38.0 mg, 0.068 mmol) as a white amorphous solid. m/z (ESI) 559.2 (M+H)+.

Provenance & Evidence