Xevo g2 qtof apparatus

The ¹H NMR and ¹³C NMR spectra were recorded using a Varian NMR system 600 spectrometer at 600 MHz in DMSO-d6, with tetramethylsilane (TMS) as the reference standard. NMR chemical shifts are reported in ppm (δ) and coupling constants (J) in Hz. Melting points were measured on a Boethius PHMK apparatus (VEB Analytik Dresden, Dresden, Germany). The progress of the reaction was monitored by thin-layer chromatography (TLC) using Merck TLC silica gel 60 F254 plates and the following developing systems: A: 5% MeOH/CHCl₃, B: 10% MeOH/CHCl₃, and C: 20% MeOH/CHCl₃. Column chromatography was conducted using silica gel 40–60 μm 60A with methanol–chloroform mixtures as eluents. Preparative high-performance liquid chromatography was performed with the LaboACE LC-5060 system (Japan Analytical Industry Co., Ltd., Tokyo, Japan), with an ODS column (JAIGEL-ODS-AP, model SP-12-10, Japan Analytical Industry, Co., Ltd. Tokyo, Japan). The compounds were eluted with a mobile phase of MeOH at a flow rate of 9 mL/min. High-resolution mass spectroscopy (HRMS) was measured on a Waters Corporation Xevo G2 QTOF apparatus (Waters Corporation, Milford, MA, USA) using electrospray ionization (ESI).

All manipulations were performed under an inert atmosphere of argon by using standard Schlenk techniques or high-pressure NMR tube techniques. Solvents were purified with an MBraun SBS-800 purification system. Dry and oxygen-free solvents were used. ¹H, ¹³C, ¹⁹F, and ³¹P NMR spectra were recorded on Brucker Avance II 300 MHz, Avance III HD 400 MHz, and Avance I and II 500 MHz spectrometers (Brucker, Karlsruhe, Germany). Chemical shifts were expressed in parts per million with residual solvent signals as internal reference (¹H and ¹³C{¹H}). ¹⁹F and ³¹P NMR chemical shifts were reported in ppm relative to CFCl₃ and 85% H₃PO₄, respectively. The following abbreviations and their combinations were used: br—broad; s—singlet; d—doublet; t—triplet; q—quartet; hept—heptuplet; m—multiplet. ¹H and ¹³C resonance signals were attributed by means of 2D COSY, HSQC, and HMBC experiments. Mass spectra were recorded on a Hewlett Packard 5989A spectrometer (Hewlett-Packard, Palo Alto, CA, USA). High-resolution MS (HRMS) spectra were realized on a Xevo G2 QTof apparatus (Waters, Milford, CT, USA). Melting points were measured in a sealed glass tube on a Stuart SMP-30 automatic melting point apparatus. All commercially available reagents were used without further purification otherwise noted. Moreover, 1 was prepared following a previously reported procedure [30 (link)].

All reagents and solvents were obtained from commercial sources and used without further purification. Reactions were monitored by TLC analysis using silica gel 60 F₂₅₄ plates (Merck, Darmstadt, Germany). Column chromatography was performed on silica gel 60 (Merck). ¹H- and ¹³C-NMR spectra were recorded on a model 600 NMR spectrometer (Varian, Palo Alto, CA, USA) at 600 and 150 MHz, respectively. Peak multiplicity is expressed as follows: s = singlet, d = doublet, t = triplet, dd = doublet of doublets. NMR chemical shifts are given in ppm (δ), relative to residual non-deuterated solvents as internal standard, coupling constants (J) are given in Hz. Melting points (mp) were determined using a Boethius PHMK apparatus (VEB Analytik, Jena, Germany) and were not corrected. High resolution electrospray ionization mass spectroscopy (ESI-HRMS) analyzes were performed using a Waters Xevo G2 Q-TOF apparatus (Waters, Milford, MA, USA).