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

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-methoxybenzyl)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (240 mg, 0.400 mmol), 2-bromo-6-cyclopropylpyrazine (CombiPhos Catalysts, Inc., Princeton, N.J.; 88 mg, 0.440 mmol), potassium phosphate (255 mg, 1.199 mmol), Pd2(dba)3 (10.98 mg, 0.012 mmol), and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos; 11.43 mg, 0.024 mmol) in dioxane (4.0 mL) and water (0.400 mL) was sparged with argon then heated at 120° C. (microwave) for 20 min. The reaction was cooled to RT, diluted with DCM (20 mL), and concentrated onto silica gel. Chromatographic purification (silica gel, 0-100% EtOAc/Hex) furnished 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (160 mg, 0.270 mmol, 68%) as a light-yellow solid: MS (ESI, pos. ion) m/z: 593.2 (M+1).

Provenance & Evidence