13523-92-7, 1-Methyl-1H-indol-5-ol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
SI-6 (Table 4, entry 6). A round bottom flask was charged with NaH (0.33 g, 8.15 mmol, 1.2 equiv, 60% dispersion in oil). A solution of N-methyl-5-hydroxyindole (SI- 5) (1.0 g, 6.79 mmol, 1 equiv) in DME (27 mL) was added dropwise via cannula to the NaH. A solution of diethylcarbamoyl chloride (0.875 mL, 6.45 mmol, 0.95 equiv) in DME (15 mL) was then added dropwise via cannula to the reaction vessel. The reaction was allowed to stir for 3.5 d, and then quenched with H20 (10 mL). The volatiles were removed under reduced pressure, and then Et20 (50 mL) and H20 (15 mL) were added. The layers were separated, and the organic layer was washed successively with 1 M KOH (20 mL) and H20 (20 mL). The combined aqueous layers were extracted with Et20 (3 x 20 mL). The combined organic layers were then washed with brine (20 mL), dried over MgS04, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (9: 1 Benzene:Et20) to yield N-methylindole-5 -carbamate SI-6 as a white solid (1.55g, 98%> yield). R 0.44 (9: 1 Benzene :Et20); 1H NMR (500 MHz, CDC13): delta 7.33 (d, J= 2.5, 1H), 7.26 (d, J = 9.0, 1H), 7.05 (d, J = 3.0, 1H), 6.98 (dd, J = 8.5, 2.3, 1H), 6.43 (dd, J = 3.0, 0.5, 1H), 3.78 (s, 3H), 3.47 (bs, 2H), 3.41 (bs, 2H), 1.27 (bs, 3H), 1.21 (bs, 3H); 13C NMR (125 MHz, CDC13): delta 155.4, 145.1, 134.5, 129.8, 128.7, 116.3, 113.2, 109.4, 101.1, 42.3, 41.9, 33.1, 14.4, 13.6; IR (film): 2972, 1708, 1467, 1418, 1218, 1159 cm”1; HRMS- ESI (m/z) [M + Na]+ calcd for Ci4Hi8N202Na, 269.1266; found, 269.1267., 13523-92-7
13523-92-7 1-Methyl-1H-indol-5-ol 10844525, aindole-building-block compound, is more and more widely used in various fields.
Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; GARG, Neil K.; RAMGREN, Stephen D.; SILBERSTEIN, Amanda L.; QUASDORF, Kyle W.; WO2012/94622; (2012); A2;,
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