Potassium Phosphate, Tribasic → N-(4-methoxybenzyl)-5-(3-(6-(2-methylpiperidin-1-yl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

K3PO4 (327 mg, 1.539 mmol) (Reidel-de Haen), XPhos (14.67 mg, 0.031 mmol) (Strem), Pd2(dba)3 (14.09 mg, 0.015 mmol) (Strem), 2-(2-methylpiperidin-1-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine (194 mg, 0.641 mmol) (CombiPhos Catalysts Inc.) and 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (308 mg, 0.513 mmol) were weighed into a 5 mL glass microwave tube. The tube was purged with argon and the contents were treated with dioxane (3.0 mL) and water (0.5 mL). The tube was sealed and the suspension was heated at 120° C. for 10 min in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden). An additional 50 mg of the boronic ester were added, the tube was sealed and the mixture was heated at 120° C. for an additional 10 min. The mixture was treated with 1N NaOH and extracted with EtOAc (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. Purification by flash chromatography (eluent: 20% MeOH in DCM) afforded N-(4-methoxybenzyl)-5-(3-(6-(2-methylpiperidin-1-yl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (177 mg, 0.272 mmol, 53.1%) as a dark yellow solid. MS (ESI, pos. ion) m/z: 650.0 (M+1).

Provenance & Evidence