Potassium Phosphate, Tribasic → methyl 6-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 5 mL glass microwave tube containing N-isopropyl-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 (120 mg, 0.230 mmol) was added methyl 2-chloro-6-cyclopropylpyrimidine-4-carboxylate (58.6 mg, 0.276 mmol), potassium phosphate (146 mg, 0.689 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (6.6 mg, 0.014 mmol), and Pd2(dba)3 (6.3 mg, 6.89 μmol). The tube was purged with argon, the solids were treated with dioxane (5 mL) and water (0.5 mL), the tube was sealed, and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 130° C. for 25 min. The mixture was treated with H2O and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (eluting with 20-100% EtOAc in Hex) affording methyl 6-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-4-carboxylate (16.4 mg, 13%) as a light yellow amorphous solid. MS (ESI, pos. ion) m/z: 397.1 (M+1).

Provenance & Evidence