Stannanecarbonitrile, tributyl- → 4-fluoro-3-[2-oxo-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]acetyl]-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile

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 tributyltin cyanide (0.07 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 16 h 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 (0.028 g). LCMS: m/e 446.2 (M+H)+, ret time 1.81 min (method 2). 1H NMR (500 MHz, DMSO-D6) δ ppm 14.06 (s, 1H) 8.66 (s, 1H) 8.50 (d, J=2.14 Hz, 1H) 7.56-7.70 (m, 5H) 3.67-3.72 (m, 2H) 3.33-3.50 (m, 4H) 3.13-3.17 (m, 2H).

Provenance & Evidence