Synthesis of 4-functionalized-1H-indoles from 2,3-dihalophenols

Roberto Sanz, Verónica Guilarte, Nuria García
2010 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
more » ... 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.
doi:10.1039/c004360e pmid:20617233 fatcat:pvr7omjvpbeqjmjhwxfx5lmv4a