Stannane, tributyl(1-ethoxyethenyl)- → HCID 49770160, 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 (0.10 g, 0.20 mmol) in 1,4-dioxane (5 mL) was added tributyl(1-ethoxyvinyl)tin (0.079 g, 0.22 mmol) followed by Pd(PPh3)4 (0.07 g, 0.06 mmol). The mixture was flushed with N2, and the tube was sealed and heated to 100° C. After 16h of heating, the mixture was cooled to rt, and the solvent was removed in vacuo. The residue was dissolved in DMF and was filtered through a pad of celite to remove any remaining solids. The DMF solution was purified by prep HPLC to give the title compound as an off-white solid (0.025 g). LCMS: m/e 463.38 (M+H)+, ret time 1.88 min (method 2). 1H NMR (500 MHz, CDCl3) δ ppm 11.02 (s, 1 H) 8.35 (s, 1 H) 8.31 (d, J=2.75 Hz, 1 H) 7.52-7.62 (m, 5 H) 3.81-3.85 (m, 2 H) 3.61-3.65 (m, 2 H) 3.39-3.43 (m, 2 H) 3.31-3.35 (m, 2 H) 2.80-2.83 (m, 3 H).

Provenance & Evidence