Mercury 400

All reactions were performed in flame-dried glassware under a positive pressure of argon. Yields refer to chromatographically and spectroscopically pure compounds, unless otherwise noted. Analytical TLC was performed on 0.25 mm glass-backed 60 Å F-254 TLC plates (Silicycle, Inc.). The plates were visualized by exposure to UV light (254 nm). Infrared spectra were recorded on a Nicolet IS5 FT-IR spectrophotometer. ¹H NMR spectra were recorded on a Varian Mercury400 and a Bruker Biospin GmbH (400 MHz) spectrometers and are reported in ppm using solvent as an internal standard (CDCl₃ at 7.26 ppm, or CD₃CN at 1.96 ppm). ¹H NMR spectra were performed using standard parameters, and data are reported as b = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet; coupling constant(s) in Hz, integration. ¹³C NMR spectra were recorded on a Varian Mercury400 (100 MHz) spectrometer. Chemical shifts are reported in ppm, with solvent resonance employed as the internal standard (CDCl₃ at 77.2 ppm, or CD₃CN at 1.3 and 118.3 ppm).

All reagents and anhydrous solvents were obtained from commercial suppliers and used without further purification. ¹H and ¹³C NMR spectra were recorded on a Varian Mercury-400, Bruker DPX-400, or DRX-500. Normal-phase chromatography was performed on a Teledyne Isco CombiFlash NextGen 300+ using Luknova SuperSep SiO₂ columns. Preparative-scale reverse phase high performance liquid chromatography (RP-HPLC) was performed on an Agilent 1260 Infinity LC system using a Gemini NX-C18 column (110 Å pore size, 5 μm particle size, 150 × 21.2 mm dimensions, mobile phase A = 0.1% TFA in H₂O, mobile phase B = 0.1% TFA in MeCN). Final compound purities were determined by analytical RP-HPLC (254 nm) and were > 95% in purity. High-resolution mass spectrometry data were collected at The Scripps Research Institute Center for Mass Spectrometry (ESI-HRMS; Agilent Technologies, LC/MSD TOF 6230).