Potassium Phosphate, Tribasic → 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added 5-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-ylboronic acid (245 mg, 0.515 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (14.7 mg, 0.031 mmol), Pd2(dba)3 (14.2 mg, 0.015 mmol), 2-bromo-6-cyclopropylpyrazine (118 mg, 0.593 mmol) (CombiPhos Catalysts Inc.) and potassium phosphate (328 mg, 1.55 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and H2O (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. The residue was purified with silica gel chromatography (eluting with 10-80% EtOAc in Hex) to give 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (191 mg, 67%) as a light yellow amorphous solid. (ESI, pos. ion) m/z: 550.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 9.01 (1H, s), 8.77 (1H, s), 8.43 (1H, s), 8.17-8.22 (2H, m), 8.11-8.16 (1H, m), 8.03 (2H, dd, J=6.6, 2.8 Hz), 7.86 (2H, d, J=8.4 Hz), 7.48-7.55 (3H, m), 7.28 (2H, d, J=8.4 Hz), 2.36 (3H, s), 2.14-2.22 (1H, m), 1.29-1.34 (2H, m), 1.17-1.24 (2H, m).

Provenance & Evidence