10075-50-0, 5-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
5-Bromoindole (1.35 g, 6.9 mmol) was formylated as described for1H-indole-3-carbaldehyde to produce 6-bromo-1H-indole-3-carbaldehyde(1.50 g, 97%) with the exception that the obtained productwas not purified by refluxing in EtOH.5-Bromo-1H-indole-3-carbaldehyde (1.50 g, 6.7 mmol) and NH4OAc(0.52 g, 6.7 mmol) were heated at reflux in CH3NO2 (18 mL, 335mmol) for 45 min, cooled to r.t., and treated with H2O (70 mL). Theproduct was extracted with EtOAc (70 mL), washed with H2O (5 ¡Á 50mL) and NaCl solution (20 mL), and dried over anhydrous Na2SO4. Thesolvent was removed in vacuo to afford 6-bromo-3-[(E)-2-nitrovinyl]-1H-indole (1.72 g, 96%, brownish crystals), which was dried in vacuoand used without further purification.A suspension of 5-bromo-3-[(E)-2-nitrovinyl]-1H-indole (1.72 g, 6.4mmol) and DMAP (0.08 g, 0.64 mmol) in anhydrous THF (7 mL) wastreated with a solution of Boc2O (2.1 g, 9.7 mmol) in anhydrous THF(7 mL) dropwise at 0-5 C over a period of 15 min, stirred at r.t. for 3h, and concentrated in vacuo. The residue was dissolved in CH2Cl2 (50mL), washed with citric acid solution (10%, 20 mL), H2O (20 mL), andconcd NaCl solution (15 mL), and dried over anhydrous Na2SO4. TheCH2Cl2 was evaporated in vacuo and the residue was purified by chromatographyon a column of silica gel (EtOAc-hexane, 6:1) to providetert-butyl 5-bromo-3-[(E)-2-nitrovinyl]-1H-indole-1-carboxylate.Yield: 2.11 g (83% from 5-bromoindole); pale-yellow solid; mp 156-157 C (MeOH); Rf = 0.55 (EtOAc-hexane, 1:8). IR (film): 3130, 2983, 2300 w, 1741 s (CO), 1639, 1509, 1452, 1368,1344, 1240, 1153, 1107, 956, 853, 803, 764, 649, 613, 579 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 8.57 (s, 1 H), 8.33 (d, J = 13.7 Hz,1 H, CH=CHNO2), 8.27 (d, J = 1.9 Hz, 1 H), 8.26 (d, J = 13.7 Hz, 1 H,CH=CHNO2), 8.02 (d, J = 8.8 Hz, 1 H), 7.56 (dd, J = 8.8, 1.9 Hz, 1 H), 1.65(s, 9 H, C(CH3)3).13C NMR (100 MHz, DMSO-d6): delta = 147.89, 136.57, 134.27, 133.94,130.89, 128.52, 128.16, 123.08, 116.83, 116.76, 111.47, 85.53, 27.48(3).MS (EI, 70 eV): m/z (%) = 368/366 (4) [M]+, 312/310 (7) [M – C4H8]+,268/266 (31) [M – C4H8 – CO2]+, 219 (21), 140 (30), 57 (100).Anal. Calcd for C15H15BrN2O4: C, 49.06; H, 4.12; N, 7.63. Found: C,49.19; H, 4.15; N, 7.55.
10075-50-0, The synthetic route of 10075-50-0 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Golantsov, Nikita E.; Festa, Alexey A.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Synthesis; vol. 49; 11; (2017); p. 2562 – 2562;,
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