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

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added 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 (86 mg, 0.167 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (4.8 mg, 9.99 μmol), Pd2(dba)3 (4.6 mg, 5.00 μmol), 2-bromo-6-cyclopropylpyrazine (CombiPhos Catalyst Inc., 36.5 mg, 0.183 mmol) and potassium phosphate (106 mg, 0.500 mmol) followed by purging with argon. The solids were treated with dioxane (3.0 mL) and water (0.3 mL) and heated in the microwave at 120° C. for 20 min. The mixture was treated with water and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification (10-100% EtOAc in Hex) afforded 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (28.1 mg, 29%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 591.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.64-8.71 (2H, m), 8.39 (1H, s), 8.13 (1H, s), 8.03 (1H, d, J=8.8 Hz), 7.81 (2H, d, J=8.4 Hz), 7.78 (1H, dd, J=8.7, 1.5 Hz), 7.54 (2H, d, J=7.6 Hz), 7.35 (2H, t, J=7.7 Hz), 7.22-7.29 (3H, m), 6.01 (1H, s), 2.35 (3H, s), 2.09-2.16 (1H, m), 1.86 (6H, s), 1.20-1.24 (2H, m), 1.08-1.14 (2H, m).

Provenance & Evidence