4-(2-(Tributylstannyl)pyrimidin-4-yl)morpholine → tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(4-morpholinopyrimidin-2-yl)-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-iodo-5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (1.2 g, 2.5 mmol) and 4-(2-(tributylstannyl)pyrimidin-4-yl)morpholine (1.38 g, 4.0 mmol) in DMF (10 mL) was added CuI (0.62 g, 3.2 mmol) and Pd(PPh3)4 (0.29 g, 0.25 mmol). The mixture was purged with Ar for 5 min then heated at 90° C. for 1 h. The mixture was poured into H2O and the aqueous layer was extracted with Et2O. The combined organic layers were dried, filtered and concentrated. The residue was purified with flash chromatography to give tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(4-morpholinopyrimidin-2-yl)-1H-indole-1-carboxylate (255 mg, 20%). MS (ESI, pos. ion) m/z: 511.1 (M+1). 1H-NMR (DMSO-d6, 300 MHz) δ: 9.12 (1H, d), 8.39 (2H, brs), 8.25 (1H, d), 7.9 (1H, dd), 6.79 (1H, d). 3.7-3.85 (8H, brs), 2.85 (3H, s), 1.65 (9H, s).

Provenance & Evidence