1,4-Dioxane → HCID 49770164, compound

Participants

Reaction Conditions

Reaction Steps

To a sealable flask containing 1-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (1.0 g, 2.0 mmol) in 1,4-dioxane (20 mL) was added tributyltin cyanide (0.70 g, 2.2 mmol) followed by Pd(PPh3)4 (0.12 g, 0.1 mmol). The mixture was flushed with N2, and the tube was sealed and heated to 100° C. After 20 h of heating, the mixture was cooled to rt, and was diluted with MeOH (50 mL) and was filtered through a pad of celite to remove solids. To the solution was added H2O (20 mL), and the mixture was heated with a heat gun. Solids formed upon cooling, and were collected by filtration. The solids were dissolved in DMF and were purified by prep HPLC to give the title compound as an off-white solid (30 mg). LCMS: m/e 464.11 (M+H)+, ret time 1.095 min (method 3). 1H NMR (500 MHz, DMSO-D6) δ ppm 12.78 (s, 1H) 8.34 (d, J=2.14 Hz, 1H) 8.30 (s, 1H) 8.25 (d, J=3.36 Hz, 1H) 7.88 (s, 1H) 7.56-7.71 (m, 5H) 3.67-3.72 (m, 2H) 3.43-3.47 (m, 2H) 3.30-3.34 (m, 2H) 3.13-3.17 (m, 2H).

Provenance & Evidence