Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1111638-02-8,5-Bromo-2-methyl-7-azaindole,as a common compound, the synthetic route is as follows.

5.1.1.4 5-Bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine (22) To a solution of compound 20 (450 mg, 2.13 mmol) in DCM (10 mL) Trifluoromethanesulfonic acid (TfOH, 1.28 g, 8.53 mmol) and 1-(2,6-Dichloro-3-fluorophenyl)ethanol (1.63 g, 8.53 mmol) was added dropwise. After stirring at 25 C under N2 for 16 h, the mixture was quenched with sat. Sodium bicarbonate (NaHCO3) solution, extracted with DCM (100 mL * 3). The organic phase was washed with water (20 mL * 2), brine (20 mL * 2), dried over Na2SO4. After filtering, the organic phase was concentrated and purified by column chromatography on silica (DCM:MeOH = 200:1) to give 22 as a white solid (650 mg, 75.8% yield). 1H NMR (400 MHz, DMSO-d6) delta 11.66 (s, 1H, NH), 8.12 (s, 1H, Ar-H), 7.87 (s, 1H, Ar-H), 7.54-7.50 (dd, J = 8.9, 5.1 Hz, 1H, Ar-H), 7.39-7.34 (t, J = 8.7 Hz, 1H, Ar-H), 5.15-5.12 (q, J = 7.4 Hz, 1H, CH), 2.18 (s, 3H, CH3), 1.86-1.83 (d, J = 7.5 Hz, 3H, CH3).

1111638-02-8, The synthetic route of 1111638-02-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Na; Wang, Yanfen; Huang, Gongchao; Ji, Conghui; Fan, Wei; Li, Haitao; Cheng, Ying; Tian, Hongqi; Bioorganic Chemistry; vol. 65; (2016); p. 146 – 158;,
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

245-08-9, 5H-Pyrido[3,2-b]indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

One 100 mLThe flask Intermediate (4) (0.5 g, 1.005 mmol), delta-carboline(d-carboline)0.2 g (1.105mmol), CuI 24 mg (0.126 mmol), 1,10 phenanthroline (1,10 phenanthroline) 45mg (0.251 mmol), cesium carbonate (cesium carbonate, Cs2CO3) 0.7 g (2.010 mmol) and dimethylformamide (dimethylformamide, DMF) (40 mL) and mixed, and then,stirred for 12 hours at 120 ~ 130C. The reaction was cooled to room temperature and then terminated and purified by silica gel column chromatography to give compound (4-33) 0.2 g (Yield: 40%) of a white solid was obtained., 245-08-9

As the paragraph descriping shows that 245-08-9 is playing an increasingly important role.

Reference£º
Patent; WS Co.,Ltd; Ko, Byung Soo; Oh, Yu Jin; (61 pag.)KR2016/50891; (2016); A;,
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

29906-67-0, 1-Methyl-5-nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Silver (I) oxide (1 eq.) was added to a stirred solution of indole (1eq.) and benzyl bromide (1 eq.) in dioxane (1 mL/mmol of indole) ina microwave tube under nitrogen gas. The reaction was sealed andstirred at 60 C for 20 h. EtOAc (2 mL/mmol of indole) was added tothe reaction. The reaction was then filtered through celite and thefiltrate was rotovapped. Product was purified by column chromatographyto give a yellow solid; 25-45%; 1H NMR (DMSO): delta 8.42 (d,J 2.3 Hz, 1H), 8.02 (dd, J 9.1, 2.3 Hz, 1H), 7.93e7.84 (m, 2H), 7.60(d, J 9.1 Hz, 1H), 7.44 (d, J 8.3 Hz, 3H), 4.21 (s, 2H), 3.83 (d,J 4.1 Hz, 6H); 13C NMR (DMSO): delta166.59, 147.18, 140.80, 140.05,132.12, 129.82, 129.25, 127.93, 126.82, 116.99, 116.29, 116.03, 110.86,52.45, 33.30, 30.65

29906-67-0, As the paragraph descriping shows that 29906-67-0 is playing an increasingly important role.

Reference£º
Article; Martinez, Anastasia A.; Espinosa, Bianca A.; Adamek, Rebecca N.; Thomas, Brent A.; Chau, Jennifer; Gonzalez, Edwardo; Keppetipola, Niroshika; Salzameda, Nicholas T.; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1202 – 1213;,
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.103858-53-3,Ethyl 6-bromoindole-2-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: To ethyl 1H-indole-2-carboxylate (1.3 g, 6.89 mmol) in THF at 0 .was added lithium aluminumhydride solution (1M, in THF 0.29 g, 1.54 mmol) dropwise and the reaction mixture was stirred for 3.5 hours at0 . The reaction mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed withTHF. Reaction mixture was dried (anhydrous Na2SO4) and evaporation of the solvent gave 1.1 g (96% yield) of thecrude (1H-indol-2-yl)methanol which was used directly in the next step.

103858-53-3, The synthetic route of 103858-53-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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.1092114-59-4,3-Iodo-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

Preparation of compound 69b: 3-iodo-l-tosyl-l/7-indole-5-carbonitrileTo a solution of 3-iodo-l//-indole-5-carbonitrile (2 g, 7.40 mmol) in DMF (20 mL) was added 60% NaH (538 mg, 22.38 mmol) portion wise at 0 C and the reaction was stirred for 10 min RT. To the above mixture at 0 C, p-TsCl (2.2 g, 11.19 mmol) solution in DMF (4 mL) was added and stirred for further 2 h at RT. The reaction was quenched with ice cold H20 (20 mL). The resulting suspension was filtered and the solid was washed with H20 (10 mL) and dried. The crude was purified with silica gel chromatography (eluent: 20% EtOAc in petroleum ether) to afford 3-iodo-l-tosyl-l//-indole-5-carbonitrile (3.0 g, 95.5%) as an off brown solid. .H NMR (400MHz, DMSO-d6): delta 8.30 (s, 1H), 8.13 (d, J=8.8Hz, 1H), 7.98 (d, J=8.4Hz, 2H), 7.87-7.81 (m, 2H), 7.43 (d, J=8.0Hz, 2H), 2.32 (s, 3H)., 1092114-59-4

As the paragraph descriping shows that 1092114-59-4 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (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

166104-19-4, tert-Butyl 5-nitro-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 2; Following the procedure set forth in Example 1 (A) above, indole derivatives were deprotected using TFE or HFIP in a microwave reactor at 150 C. as set forth in Table 1 below., 166104-19-4

As the paragraph descriping shows that 166104-19-4 is playing an increasingly important role.

Reference£º
Patent; Roch Palo Alto LLC; US2009/203910; (2009); 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

6146-52-7,6146-52-7, 5-Nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Nitro-lH-indole (325 mg, 2.0 mmol)In dichloromethane (6 mL) was added di-tert-butyl dicarbonateEster (524 mg, 2.4 mmol),Stirred at 0 C for 5 minutes,A further catalytic amount of 4-dimethylaminopyridine (3 mg, 0.025 mmol) was added,Stirring is then continued for 30 minutes at room temperature.Quenched by adding water (2 mL)Extract with dichloromethane (15 mL x 3).The combined organic phase was washed with water (20 mL)Saturated brine (15 mL ¡Á 2)Dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure,Obtained as a gray solid (526 mg, 100%),Directly used for the next reaction.

As the paragraph descriping shows that 6146-52-7 is playing an increasingly important role.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wen Liang; Zheng Jinfu; Zhang Jin; Wu Shoutao; Yuan Xiaofeng; Lin Runfeng; Wang Xiaojun; Zuo Yinglin; Zhang Yingjun; (21 pag.)CN104311541; (2017); B;,
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.169674-57-1,5-Chloro-6-fluoro-1H-indole,as a common compound, the synthetic route is as follows.

10 g (68.7 mmol) of 4-chloro-3-fluoro-phenylamine were dissolved in 38 ml dichloro-methane and treated with a solution of 6.82 g (72.1 mmol) of sodium bicarbonate in water (110 ml). At RT 8 ml (103 mmol) of methyl chloroformate were added dropwise over a period of 25 min (temperature rise from 22 to 28 C.). After stirring for 1.5 h at RT, the reaction mixture was diluted with dichloromethane (100 ml). After phase separation, the organic layer was washed with brine (45 ml), dried with magnesium sulfate, filtered and diluted with hexane (140 ml). The dichloromethane was then removed in vacuo and the resulting suspension filtered leading to 13 g (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester as a white powder (92%). MS (El) 203.1 (M)+.5.34 g (26.2 mmol) of (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester were dissolved in acetonitrile (50 ml) and treated with 6.49 g (28.85 mmol) of N-iodosuccinimide and 0.23 ml (2.62 mmol) of trifluoromethanesulfonic acid under nitrogen and stirred at RT for 3 hours. The reaction mixture was then poured into 50 ml of saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic extracts were then washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 8.2 g of (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester (95%) as a dark blue powder. MS (EI) 328.9 (M)+.153 mg (0.22 mmol) of Pd(PPh3)2Cl2 and 42 mg (0.22 mmol) of CuI were dissolved in 40 ml of triethylamine under argon and the mixture was heated to reflux for 20 min. The reaction mixture was then cooled to 0 C. and 7.2 g (21 mmol) of (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester were added. After 10 min stirring at RT, 3.45 ml (24.9 mmol) of ethynyltrimethylsilane were added dropwise (exothermic, temperature rise from 18 to 33 C.) and the reaction mixture was stirred for one hour at RT. The mixture was then poured into 180 ml of aqueous 1N HCl and ice and extracted with ethyl acetate. The organic extracts were then washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining crude material (ca 21 mmol) was dissolved in THF (200 ml) and treated with 43.3 ml (43.3 mmol) of tetrabutylammonium fluoride (1M in THF) at RT. After 5 min stirring at RT, the reaction mixture was refluxed for one hour under argon. The reaction mixture was then cooled to RT and concentrated in vacuo. The resulting oil was treated with water (55 ml), stirred for 10 min and finally extracted with ethyl acetate. The combined organic layers were sequentially washed with 1M HCl (50 ml), saturated sodium bicarbonate (50 ml), brine (50 ml) and finally dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining residue was suspended in hexane (200 ml) and-the mixture was heated to reflux, then cooled to 5 C. and the solid was collected by filtration leading to 3.15 g of 5-chloro-6-fluoro-1H-indole as a light brown solid (85%). MS (EI) 169.1 (M)+.35 ml of THF were cooled to -75 C. and 19.05 ml (30.5 mmol) of a 1.6M solution of n-butyllithium in hexane were added under argon. Then a solution of 2.35 g (13.7 mmol) of 5-chloro-6-fluoro-1H-indole in THF (9 ml) was added dropwise (temperature kept between -70 and -75 C.) over 15 min. After 5 additional min of stirring at this temperature a solution of 3.7 g of potassium tert-butylate in THF (15 ml) was added over period of 10 min (temperature kept between -70 and -75 C.). The resulting brown solution was then stirred for 2 hours at the same temperature and treated with a large excess of solid CO2. The temperature was then raised to 10 C. over a period of 75 min and water (30 ml) was added to the reaction mixture. After separation of the organic layer, the aqueous layer was extracted with ether and treated with concentrated HCl to adjust the pH to 1. The resulting suspension was then filtered and the solid was washed with water and dried in high vacuo. The remaining residue was suspended in 10 ml of hexane/ether 9:1 and stirred for 15 min, filtered off, washed with 5 ml of the same solvent mixture and was dried in high vacuo, leading to 2.2 g of 5-chloro-6-fluoro-1H-indole-7-carboxylic acid as a light brown solid (75%). MS: 212.2 (M-H)-

169674-57-1, The synthetic route of 169674-57-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Faeh, Christoph; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Pflieger, Philippe; US2007/185113; (2007); 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.74420-02-3,4-Hydroxy-7-azaindole,as a common compound, the synthetic route is as follows.,74420-02-3

A solution of 1 ,2,3-trifluoro-5-nitrobenzene (CAS No. [66684-58-0]; 3.59 g, 20.3 mmol) and 1 H- pyrrolo[2,3-b]pyridin-4-ol (CAS No. [74420-02-3]; 1 .10 eq., 2.99 g, 22.3 mmol) in DMSO (65 mL) was treated with potassium carbonate (4.00 eq, 1 1 .2 g, 81.1 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (3 x 200 mL) and brine (150 mL), dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (S1O2- hexane/ ethyl acetate) to give the title compound (3.1 g, 52percent). LC-MS (method 2): Rt = 1 .13 min; MS (ESIpos): m/z = 292 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) delta [ppm] = 6.35 (d, 1 H), 6.59 (d, 1 H), 7.47 (d, 1 H), 8.13 (d, 1 H), 8.37 – 8.43 (m, 2H), 1 1 .97 (br s, 1 H).

As the paragraph descriping shows that 74420-02-3 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM HEIDELBERG; BAYER AKTIENGESELLSCHAFT; BUCHMANN, Bernd; SCHMEES, Norbert; MOWAT, Jeffrey Stuart; LEDER, Gabriele; PANKNIN, Olaf; CARRETERO, Rafael; AIGUABELLA FONT, Nuria; BRIEM, Hans; FRIBERG, Anders Roland; HUSEMANN, Manfred; BOeMER, Ulf; STOeCKIGT, Detlef; NEUHAUS, Roland; BERNDT, Sandra; PETERSEN, Kirstin; OFFRINGA, Rienk; (494 pag.)WO2018/228920; (2018); 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