With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4769-96-4,6-Nitro-1H-indole,as a common compound, the synthetic route is as follows.
Camphorsulfonic acid (CSA) (6.9 mg, 0.03 mmol), the indolederivative (0.30 mmol) and hypervalent iodine reagent (119.4 mg,0.33 mmol) were placed into an oven-dried sealed bomb equippedwith a stirring bar under Ar. Under a positive ow of argon, 1.5 mLof freshly distilled 1,2-dichloroethane was added. The reaction wasstirred at 40 8C and monitored by 19F NMR spectroscopy until thedisappearance of the electrophilic triuoromethylthiolating re-agent 3 (typically 24 h). 15 mL of brine and 10 mL of CH2Cl2 wasadded and the organic phase was separated. The aqueous phasewas extracted with CH2Cl2 (3 10 mL) and the combined organicextracts were dried over anhydrous Na2SO4, and concentrated in vacuo. 3-(Triuoromethylthio)-1H-indole-5-carbonitrile (Table 2, en-try 11). Yield 78%, yellow solid, m.p. 156-158 8C. 1H NMR(400 MHz, ACETONE-D6, 293 K, TMS) d 11.43 (s, 1H), 7.98 (s,1H), 7.93 (d, J = 2.8 Hz, 1H), 7.61 (dd, J = 8.4, 0.8 Hz, 1H), 7.44 (dd,J = 8.4, 1.6 Hz, 1H) ppm; 19F NMR (376.4 MHz, ACETONE-D6) d45.70 (s, 3F) ppm; 13C NMR (100.7 MHz, ACETONE-D6, 293 K,TMS) d 138.53, 137.14, 131.01 (q, J = 309.6 Hz), 129.39, 125.61,123.74, 119.51, 113.87, 104.60, 94.22 (q, J = 2.5 Hz) ppm. MS (EI):m/z (%) 242, 173 (1 0 0). HRMS: Calculated for C10H5N2F3S:242.0126; Found: 242.0128.
4769-96-4, 4769-96-4 6-Nitro-1H-indole 78502, aindole-building-block compound, is more and more widely used in various.
Reference£º
Article; Ma, Bingqing; Shao, Xinxin; Shen, Qilong; Journal of Fluorine Chemistry; vol. 171; (2015); p. 73 – 77;,
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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