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

Participants

Reaction Conditions

Reaction Steps

N-(2-Phenylpropan-2-yl)-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 (757.3 mg, 1.265 mmol), 2-bromopyrimidine (221 mg, 1.392 mmol) (Aldrich), potassium phosphate (806 mg, 3.80 mmol) (Sigma-Aldrich), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (36.2 mg, 0.076 mmol) (Strem Chemicals), and Pd2(dba)3 (34.8 mg, 0.038 mmol) (Strem Chemicals) were weighed into a 20 mL glass microwave tube, and the tube was purged with argon. The solids were treated with dioxane (8 mL) and water (0.800 mL), the tube was sealed and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. The mixture was treated with water, extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (30-100% EtOAc in Hex) to give N-(2-phenylpropan-2-yl)-5-(3-(pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (297.4 mg, 0.540 mmol, 42.7%). MS (ESI, pos. ion) m/z: 551.2 (M+1).

Provenance & Evidence