Synthesis of 4-functionalized-1H-indoles from 2,3-dihalophenols
Organic and biomolecular chemistry
Index General information S1 Experimental procedures and characterization data for synthesized compounds S2 References S15 Spectra S17 General information All reactions involving air-sensitive compounds were carried out under a N 2 atmosphere in oven-dried glassware with magnetic stirring. Temperatures are reported as bath temperatures. Solvents used in extraction and purification were distilled prior to use. TLC was performed on alumina-backed plates coated with silica gel 60 with F 254
... or; the chromatograms were visualized by UV light (254 nm) and/or by staining with a Ce/Mo reagent, anisaldehyde or phosphomolybdic acid solution and subsequent heating. R f values refer to silica gel. Flash column chromatography was carried out on silica gel 60, 230-400 mesh. Melting points were obtained with open capillary tubes and are uncorrected. 1 H NMR spectra were recorded at 400 or 300 MHz. Chemical shifts are reported in ppm from tetramethylsilane with the residual solvent resonance as the internal standard (CHCl 3 : δ 7.26). Data are reported as follows: chemical shift, multiplicity (s: singlet, br s: broad singlet, d: doublet, dd: doublet of doublets, dt: doublet of triplets, ddd: doublet of doublet of doublets, t: triplet, t app: apparent triplet, td: triplet of doublets, tdd: triplet of doublet of doublets, q: quartet, m: multiplet), coupling constants (J in Hz) and integration. 13 C NMR spectra were recorded at 100.6 or 75.4 MHz using broadband proton decoupling. Chemical shifts are reported in ppm with the solvent resonance as internal standard (CDCl 3 : δ 77.16). Carbon multiplicities were assigned by DEPT techniques. GC-MS analysis and low-resolution electron impact mass spectra (EI-LRMS) were obtained at 70 eV on a mass spectrometer and only the molecular ions and/or base peaks as well as significant peaks in MS are given. High-resolution mass spectrometry (HRMS) was carried out on a mass spectrometer. Infrared spectra were recorded with a FT-IR spectrophotometer. Melting points were measured on a Gallenkamp apparatous using open capillary rubes and are uncorrected. All commercially available reagents were used without purification unless otherwise indicated and were purchased from standard chemical suppliers.