Month: March 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, Oxalyl chloride (1.55 mL, 18.3 mmol) was added to a suspensionof the above acid (2.48 g, 15.3 mmol) in DCM (100 mL, anhydrous)and DMF (0.05 mL, 0.64 mmol) at 20 C. The mixture wasstirred at 20 C for 1 h to give a colourless solution which wascooled to 0 C. N,O-Dimethylhydroxylamine hydrochloride (1.64g, 16.8 mmol) and pyridine (3.71 mL, 45.9 mmol) were addedsequentially and the mixture was stirred at 20 C for 18 h, thenpartitioned between EtOAc and sat. aq. NaHCO3. Column chromatographywith 95:5 DCM:EtOAc gave N-methoxy-N-methylbenzofuran-5-carboxamide (2.28 g, 73%) as a pale brown oil. 1H NMR(CDCl3) d 7.99 (d, J = 1.4 Hz, 1H), 7.65-7.69 (m, 2H), 7.52 (dt, J =8.6, 0.6 Hz, 1H), 6.82 (dd, J = 2.2, 0.9 Hz, 1H), 3.56 (s, 3H), 3.39 (s,3H). Found: [M+H] = 206.2.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
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.81779-27-3,4-Hydroxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.,81779-27-3

EXAMPLE 2 OF REFERENCE 3-Formyl-4-hydroxyindole-1-carboxylic Acid tert-butyl Ester (2-1) (R7=R11=H) A mixture of the 3-formyl-4-hydroxyindole (1-1) 323 mg, di-tert-butyldicarbonate 458 mg, dimethylaminopyridine 12.5 mg and acetonitrile 25 ml was stirred under cooling in ice for 3 h.The solvent was removed under reduced pressure and the residue obtained was recrystallized from acetone-isopropyl ether to give the titled compound as pale yellow crystals, m.p. 159-161 C.(dec.), 389 mg.Yield 74%. 1H-NMR(CDCl3): 1.71 (9H, s), 6.84 (1H, dd, J=8.1, 0.9 Hz), 7.31 (1H, t, J=8.1 Hz), 7.61 (1H, dd, J=8.1, 0.9 Hz), 8.25 (1H, s), 9.76 (1H, d, J=0.6 Hz), 10.13 (1H, s).

81779-27-3 4-Hydroxy-1H-indole-3-carbaldehyde 9815282, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Fukui, Yoshikazu; Adachi, Makoto; Sasatani, Takashi; US2003/236295; (2003); 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

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Furthermore, 7-benzyloxyindole (404 mg, 1.81 mmol) was hydrogenated over 10% palladium on carbon (40 mg) in EtOH (4.2 mL) at ambient temperature under atmosphere pressure for 6 h. The catalyst was filtered off and washed with EtOH. The filtrate was concentrated to give 7-hydroxyindole as pale purple crystals, which was rapidly and directly used for the next reaction., 20289-27-4

The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Brigham and Women’s Hospital, Inc.; President and Fellows of Harvard College; US2005/119260; (2005); 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

14618-45-2, 3-(Trifluoroacetyl)indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of product of Step A (0.55 g, 2.58 mmol), K2CO3 (0.43 g, 3.1 1 mmol) and propyrgyl bromide (2 ml) in anhydrous DMF (8 ml), was stirred for 4 h. The mixture was quenched with NH4CI solution and diluted to 50 ml with EtOAc. The organic layer separated and washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to give the title compound (0.57 g, 88%), as yellow crystalline material. 1H-NMR (CDCI3) 8.41 – 8.38 (b, 1 H); 7.99 (s, 1 H); 7.48 – 7.31 (m, 3H); 4.96 (d, 2H, J = 2.55 Hz); 2.58 (t, 1 H, J = 2.55 Hz).

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AKAAL PHARMA PTY LTD; GILL, Gurmit S; GROBELNY, Damian W; WO2010/43000; (2010); 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

434958-85-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.

Step 4: 1H-indole-1-carboxylic acid 5-[(dichlorophosphinyl)oxy]-1,1-dimethylethyl ester; To tert-butyl 5-hydroxy-1H-indole-1-carboxylate in Et2O (0.11 M) was added TEA (1.0 eq.), this solution was cooled to -78 C., then phosphorous oxychloride (1.0 eq) was added neat at that temperature and the resulting solution was left to warm to room temperature overnight. The white slurry was filtered under an inert atmosphere of N2 and all volatiles removed to yield the title compound as a colorless liquid that was used as is for the next step.31P NMR (300 MHz, CDCl3, 300K): delta4.23.

434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; MacCoss, Malcolm; Olsen, David B.; Donghi, Monica; Gardelli, Cristina; Harper, Steven; Meppen, Malte; Narjes, Frank; Pacini, Barbara; US2010/234316; (2010); 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

525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the 3-bromo-5-nitro-1H-indole (200 mg, 0.83 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (267 mg, 0.91 mmol) in THF (10 mL) was added Na2CO3 (175 mg, 1.7 mmol) in H2O (3 mL). The mixture was degassed and refilled with nitrogen for 3 times. Then Pd (PPh3)2Cl2 (47 mg, 0.065 mmol) was added to the above mixture and the mixture was degassed for another 3 times. The mixture was heated to reflux for overnight. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate. The combined organic layer was dried (Na2SO4), and concentrated to get crude product, which was purified by column chromatography on 100-200 mesh silica gel to afford the title compound (100 mg, 37%) as yellow solid. 1H NMR (400 MHz, CDCl3): delta ?81 (d, J=1.2 Hz, 1H), 8.50 (br.s, 1H), 8.14-8.17 (dd, J=2.0, 8.8 Hz, 1H), 7.56 (s, 1H), 7.36-7.46 (m, 3H), 6.53-6.52 (m, 1H), 1.65 (s, 9H). LCMS: m/e 327.85 [M+H]+, 525593-33-3

The synthetic route of 525593-33-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (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

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k).

399-51-9, As the paragraph descriping shows that 399-51-9 is playing an increasingly important role.

Reference：
Article; Zheng, Jing; Deng, Lijuan; Chen, Minfeng; Xiao, Xuzhi; Xiao, Shengwei; Guo, Cuiping; Xiao, Gaokeng; Bai, Liangliang; Ye, Wencai; Zhang, Dongmei; Chen, Heru; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 158 – 167;,
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

380448-07-7, 5-Chloro-3-formyl-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[Referential Example 287] 5-Chloro-2-ethoxycarbonylindole-3-carboxylic acid: The compound (1.5 g) obtained in Referential Example 286 and sulfamic acid (1.7 g) were dissolved in tert-butanol (30 ml)-water (30 ml), and sodium chlorite (1.6 g) was added to stir the mixture for 8 hours.. The reaction mixture was diluted with water and extracted with ethyl acetate, and the extract was successively washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate.. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and hexane to obtain the title compound (0.7 g).1H-NMR (DMSO-d6) delta: 1.34(3H,t,J=7.1Hz), 4.38(2H,q,J=7.1Hz), 7.33(1H,dd,J=8.0,1.4Hz), 7.52(1H,d,J=8.0Hz), 7.97(1H,d,J=1.4Hz), 12.75(1H,br).

380448-07-7, 380448-07-7 5-Chloro-3-formyl-1H-indole-2-carboxylic acid 4714969, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1405852; (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.900514-08-1,5-Chloro-3-iodo-7-azaindole,as a common compound, the synthetic route is as follows.

900514-08-1, Example 26: Synthesis of 5-chloro-3-iodo-l-triisopropylsilanyl-lH-pyrrolo|2,3-b]pyridine 144[0234] 5-Chloro-3-iodo-l -tnisopropylsilanyl-lH-pyrrolo[2,3-b]pyridine 144 was synthesized in one step from 5-Chloro-3-iodo-lH-pyrrolo[2,3-b]py?dine 150 as shown in Scheme 49Scheme 49Step I – Preparation oj 5~Chloro-3-iotaodo-l-trusopropylsiotalanyl-lH-pvrrolo[2,3-b] pyridine (144) [0235] 5-Chloro-3-iodo-lH-pyrrolof2,3-b]pyridine (150, 31 2 g, 0 112 mol) was dissolved in N- methylpyrrohdinone (800 mL) and NaH (60% dispersion, 4 93 g, 0 123 mol) was added at room temperature The resulting mixture was stirred for 30 minutes To this mixture was then added t?isopropylsilylchlo?de (24 0 mL, 0 1 12 mol) and the resulting mixture was stirred for 2 hours The reaction was quenched with water and extracted with ethyl acetate three times, washed by brmc, dried, filtered, and concentrated in vacuo The residue was subjected to silica gel flash chromatography (eluted by heptane to 5% ethyl acetate/heptane) to afford the desired compound (43 g, 88 %) as a pale-yellow solid.

900514-08-1 5-Chloro-3-iodo-7-azaindole 24229220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

Intermediate-1: N-(lH-indol-5-yl)pivalamideTo a stirred solution of 5-Indole amine (0.6 g, 4.54 mmol) in anhydrous dichloromethane (15 mL), triethylamine (1.3 mL, 9.0 mmol) and pivaloyl chloride (0.45 mL, 5.4 mmol) were added and stirred at room temperature for 2 h. The reaction mixture was diluted with water; the organic layer was separated and concentrated in vacuo. The resultant residue was purified by flash column chromatography to give N-(lH-indol-5-yl)pivalamide (0.88g, 89%); MS: 217.0 (M+l).

5192-03-0, As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; LUPIN LIMITED; THOTAPALLY, Rajesh; KACHI, Onkar, Gangaram; RODGE, Atish, Harishchandra; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/69917; (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