Potassium Carbonate → 4-(6-(5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with tert-butyl 3-(6-morpholinopyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (250 mg, 0.495 mmol) and 2,5-dibromo-1,3,4-thiadiazole (133 mg, 0.544 mmol) in p-dioxane/H2O (4:1, 4.5 mL) followed by potassium carbonate (205 mg, 1.484 mmol) and Pd(PPh3)4 (28.6 mg, 0.025 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 75 min. The mixture was diluted with DCM, washed with H2O, dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 2-10% EtOAc in DCM) to give 4-(6-(5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)morpholine (36.0 mg, 0.081 mmol, 16.45%) as a yellow solid. MS (ESI, pos. ion) 442 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (1H, br. s.), 9.11 (1H, d, J=1.6 Hz), 8.19 (1H, d, J=2.5 Hz), 7.80 (1H, dd, J=8.6, 1.8 Hz), 7.56-7.64 (2H, m), 7.24 (1H, d, J=7.4 Hz), 6.67 (1H, d, J=8.4 Hz), 3.79-3.86 (4H, m), 3.58-3.65 (4H, m).

Provenance & Evidence