Potassium Phosphate, Tribasic → 2-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-5-isobutyl-1,3,4-oxadiazole

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added 2-isobutyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (233 mg, 0.530 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15.2 mg, 0.032 mmol), Pd2(dba)3 (14.6 mg, 0.016 mmol), 2-bromo-4-cyclopropylpyrimidine (CombiPhos Catalysts Inc., 121 mg, 0.610 mmol) and potassium phosphate (338 mg, 1.59 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and water (0.4 mL) and heated in the microwave at 130° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification (eluting with 10-60% EtOAc in Hex) afforded 2-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-5-isobutyl-1,3,4-oxadiazole (108 mg, 40%) as a light yellow viscous oil. MS (ESI, pos. ion) m/z: 514.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 9.27 (1H, s), 8.50-8.58 (2H, m), 8.09-8.13 (2H, m), 7.86 (2H, d, J=8.4 Hz), 7.24 (2H, s), 7.07 (1H, d, J=5.1 Hz), 2.84 (2H, d, J=7.2 Hz), 2.35 (3H, s), 2.29 (1H, s), 1.91 (1H, br. s.), 1.34-1.40 (2H, m), 1.17 (2H, dd, J=7.8, 2.9 Hz), 1.07 (6H, d, J=6.7 Hz).

Provenance & Evidence