Category: 4769-96-4

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.,4769-96-4

A solution of 6-nitro-1H-indole (1.0 g, 6.17 mmol) in tetrahydrofuran (5 mL) cooled to 0 C. was treated with trifluoroacetic anhydride (1.31 mL, 9.25 mmol). The reaction was stirred at 0 C. for 1 h and then was allowed to warm to 25 C. where it was stirred for 16 h. At this time, the reaction was poured into water (100 mL) and stirred at 25 C. for 5 min. The resulting precipitate was collected by filtration, washed with water (100 mL), and dried in vacuo. This solid was re-dissolved in tetrahydrofuran (8 mL) at 25 C., and the resulting solution was treated with trifluoroacetic anhydride (1 mL, 7.08 mmol) and was stirred at 25 C. for 1 h. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone (646 mg, 40%) as a yellow solid: mp 263-265 C.; EI-HRMS m/e calcd for C10H5F3N2O3 (M+) 258.0252, found 258.0253. [0060] A solution of 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone (1.0 g, 3.87 mmol) in N,N-dimethylformamide (10 mL) at 25 C. was treated with potassium carbonate (1.34 g, 9.68 mmol). The resulting mixture was stirred at 25 C. for 10 min and then treated with 2-iodopropane (0.58 mL, 5.81 mmol). The reaction was heated at 65 C. for 3 h. At this time, the reaction was cooled to 25 C. and was partitioned between water (50 mL) and ethyl acetate (50 mL). This mixture was treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1¡Á50 mL) and a saturated aqueous sodium chloride solution (1¡Á50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (581 mg, 98%) as a yellow solid: mp 143-145 C.; EI-HRMS m/e calcd for C14H14F3NO (M+) 269.1027, found 269.1037. [0061] A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (525 mg, 1.75 mmol) in a 20% aqueous sodium hydroxide solution (10 mL) was heated at 1110 C. for 2 h. At this time, the reaction was cooled to 25 C., partitioned between water (75 mL) and ethyl acetate (75 mL), and treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1¡Á50 mL) and a saturated aqueous sodium chloride solution (1¡Á50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (436 mg, 99%) as a yellow solid: mp 242-243 C.; EI-HRMS m/e calcd for C12H12N2O4 (M+) 248.0797, found 248.0796. [0062] A solution of 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (200 mg, 0.81 mmol) in methylene chloride (4 mL) and NN-diisopropylethylamine (0.32 mL, 1.85 mmol) at 25 C. was treated with benzotriazol-1-yloxy-tris(dimethylamino) phosphonium hexafluoro-phosphate (463 mg, 1.05 mmol). The reaction was stirred at 25 C. for 20 min. At this time, the reaction was treated with 2-aminothiazole (186 mg, 1.85 mmol) and was stirred at 25 C. for 24 h. At this time, the reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL) and was treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was dissolved in a hot solution of 1/1 hexanes/ethyl acetate and then filtered. The filtrate was cooled in the freezer for 1 h. At this time, the resulting solid was collected by filtration. The filtrate was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/1 hexanes/ethyl acetate) afforded 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid thiazol-2-ylamide (13 mg, 4.9%) as a yellow solid: mp 236-239 C.; EI-HRMS m/e calcd for C15H14N4O3S (M+) 330.0786, found 330.0792.

As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Patent; Corbett, Wendy Lea; US2004/67939; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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.

To a mixture of 6-nitroindole (1 g, 6.2 mmol), zinc triflate (2.06 g, 5.7 mmol) and TBAI (1.7 g, 5.16 mmol) in anhydrous toluene (11 mL) was added DIEA (1.47 g, 11.4 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 10 min at 120 C., followed by addition of t-butyl bromide (0.707 g, 5.16 mmol). The resulting mixture was stirred for 45 min at 120 C. The solid was filtered off and the filtrate was concentrated to dryness and purified by column chromatography on silica gel (Pet.Ether./EtOAc 20:1) to give 3-tert-butyl-6-nitro-1H-indole as a yellow solid (0.25 g, 19%). 1H NMR (CDCl3) delta 8.32 (d, J=2.1 Hz, 1H), 8.00 (dd, J=2.1, 14.4 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.25 (s, 1H), 1.46 (s, 9H).

4769-96-4, As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Patent; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

4769-96-4, 6-Nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of compounds 1-4 (6.13 mmol) in ethanol (30 mL) was treated with 10% Pd/C (20 wt. %of 1-4) and subjected overnight to 50 psi H2 (g) in a Parr hydrogenation apparatus. The reaction mixture was filtered and concentrated in vacuo. Pure products 1M-4M were obtained via flash chromatography by eluting with a gradient of 30%-40% EtOAc/hexanes.

4769-96-4, As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Article; Zhang, Da-Jun; Sun, Wen-Fang; Zhong, Zhao-Jin; Gao, Rong-Mei; Yi, Hong; Li, Yu-Huan; Peng, Zong-Gen; Li, Zhuo-Rong; Molecules; vol. 19; 1; (2014); p. 925 – 939;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

4769-96-4, 6-Nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[000423j To a stirred solution of compound 1 (1 g, 1 eq) in DMF (10 mL), NaH (0.22 1 g,1.5 eq) was added at 0 C followed by the addition of methyl iodide (2.3 mL, 3 eq) at same temperature. The reaction mixture was stirred at same temperature for 30 mm. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (3 X 25 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 2.

4769-96-4, As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

4769-96-4,4769-96-4, 6-Nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(a) Step 1 6-Nitroindole (1.0 g, 6.2 mmol) was successively added with acetic acid (2.5 mL), water (5.0 mL), and hexamethylenetetramine (1.2 g, 8.4 mmol), and then the mixture was stirred overnight at 120C in a sealed tube. The reaction mixture was added with water, and the precipitated solid was collected by filtration, and then dried to obtain 6-nitro-1H-indole-3-carboxaldehyde (0.91 g, 77%). 1H NMR (300 MHz, DMSO-d6) delta 8.12 (d, J = 8.8 Hz, 1H), 8.27 (d, J = 8.8 Hz, 1H), 8.44 (s, 1H), 8.66 (s, 1H), 10.02 (s, 1H).

The synthetic route of 4769-96-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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.,4769-96-4

AddiV-bromosuccinamide (NBS) to 6-nitroindole 1 (22.72 g, 140.12 mmol) dissolved in tetrahydrofuran (600 mL) and allow the resulting mixture to stir for 18 hours. Quench the reaction mixture with saturated aqueous sodium thiosulfate solution (600 mL), dilute with ethyl acetate (EtOAc) (600 mL), and separate the layers. Sequentially, wash the organic layer with saturated aqueous sodium bisulfate (100 mL), saturated aqueous sodium bicarbonate (100 mL), water (100 mL), and brine (100 mL). Dry the resulting organic layer over Na2SO4 and filter. Concentrate the filtrate to give a yellow solid. Recrystallize the solid from dichloromethane and hexane to give 29.21 g of the title compound (86 %). LRMS (API ES+) = 263.0 (M+Na).

The synthetic route of 4769-96-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/87488; (2007); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

4769-96-4, 6-Nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 6-Aminoindole was prepared from 6-nitroindole in a manner similar to that described in Example 5b.

4769-96-4, 4769-96-4 6-Nitro-1H-indole 78502, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; US6228877; (2001); B1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles