69047-36-5, 1-Methyl-1H-indole-7-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
A solution of 6a (549 mg, 0.88 mmol) in anhydrous tetrahydrofuran (8 mL) at -78 C was treated dropwise with LiHMDS (1.3 mL, 1.30 mmol) and stirred at the same temperature for 0.3 h. A solution of indole-7-carboxyaldehyde (293 mg, 1.83 mmol) in anhydrous tetrahydrofuran (1 mL) was added dropwise, and the mixture was stirred at -78 C for 2 h. A saturated aqueous solution of NH4Cl (15 mL) was added at room temperature and the aqueous phase was extracted with ethyl ether (3 * 20 mL). The organic phase was dried (Na2SO4) and concentrated to give a mixture of diastereomers, which was used directly in the next step. Thus, the residue was dissolved in anhydrous dichloromethane (6 mL) and treated with triethylamine (0.54 mL, 3.52 mmol) and MsCl (0.14 mL, 1.76 mmol) at 0 C for 2 h. DBU (0.66 mL, 4.4 mmol) was added and the mixture was allowed to reach room temperature for 2 h. The reaction was quenched by the addition of NH4Cl (ss, 10 mL) and the aqueous phase was extracted with CH2Cl2 (3 * 20 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by silica gel flash column chromatography (gradient 0-20% EtOAc/hexanes) to give 528 mg (78% yield) of 7a as a colorless syrup.
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Article; Garcia, Lia C.; Donadio, Lucia Gandolfi; Mann, Ella; Kolusheva, Sofiya; Kedei, Noemi; Lewin, Nancy E.; Hill, Colin S.; Kelsey, Jessica S.; Yang, Jing; Esch, Timothy E.; Santos, Marina; Peach, Megan L.; Kelley, James A.; Blumberg, Peter M.; Jelinek, Raz; Marquez, Victor E.; Comin, Maria J.; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3123 – 3140;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
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