Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219552-64-4,tert-Butyl 6-nitro-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 2.Synthesis of 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester 6-Nitro-indole-1-carboxylic acid t-butyl ester (1 eq) was dissolved in methanol (0.1M), to this solution was added palladium on carbon (0.1 eq) in methanol under nitrogen.A hydrogen atmosphere was then inserted and resulting mixture allowed to stir for 3 hours at room temperature.The reaction mixture was then filtered through celite and solvent removed in vacuo to afford 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester as a white solid. MS: MH+235, 219552-64-4

219552-64-4 tert-Butyl 6-nitro-1H-indole-1-carboxylate 22240526, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (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, To 5-chloro-3-iodo- 1H-pyrrolo[2,3-b]pyridine (2, 16.50 g,59.25 mmol) in 250.0 mE of N,N-dimethylformamide, sodium hydride (3.10 g, 60% in mineral oil, 77.5 mmol) was added. The reaction was stirred at room temperature for 90 minutes, then triisopropysilyl chloride (3, 13.00 mE, 61.36 mmol) was added slowly. The reaction was stirred at room temperature overnight, then poured into water and extractedwith ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel colunm chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated undervacuum to provide the desired compound (4, 10.0 g). 5-fluoro-3-iodo-1 -triisopropylsilanyl-1 H-pyrrolo[2,3-b]pyridine is prepared similarly from 5-fluoro-3-iodo-1H-pyrrolo [2,3-b]pyridine.3-Iodo-5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 5,3-iodo-5-trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 6, and 3-iodo-4-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 73-Iodo-5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 5,3-iodo-5-trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 6, and 3-iodo-4-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 7

The synthetic route of 900514-08-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Plexxikon Inc.; Zhang, Jiazhong; Ibrahim, Prabha N.; Bremer, Ryan; Spevak, Wayne; Cho, Hanna; US9096593; (2015); B2;,
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.400071-95-6,5-Bromo-1-methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.,400071-95-6

In a dry flask under argon, the carboxylic acid (2m) (100 mg, 0.39 mmol) was dissolved in dry dichloromethane (3 mL) and few drops of dry DMF. The sluggish solution was cooled to 0 C and freshly distilled oxalyl chloride (60 mg, 0.47 mmol) was added dropwise. The mixture was then stirred for 4 hours at room temperature and directly evaporated with toluene under reduced pressure. The desired acid chloride was obtained as a yellow solid and used straightaway.

The synthetic route of 400071-95-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Universite Joseph Fourier; Denis, Jean-Noel; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Jeanty, Matthieu; EP2548864; (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

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

14618-45-2, To a stirred solution of t-butylmethylamine (2.8 mL, 23.5 mmol, 5 eq.), in THF (40 mL) at 0 C under nitrogen was added slowly n-BuLi (9.4 mL, 23.5 mmol, 2.5 M in hexanes, 5 eq.). The solution was stirred at 0 C for 2 h. To the anion was added 3-trifluoroacetylindole (6) (1.0 g, 4.69 mmol, 1 eq.) in THF (40 ml) at 0 C. The reaction mixture was allowed to gradually warm to rt over 18 h then poured onto ice H2O (75 mL) and stirred for 4 h. The aqueous solution was extracted with CH2Cl2 (4 x 75 mL). The organic extracts were combined, washed with brine (2 x 50 mL), dried (Na2SO4), and concentrated in vacuo to give a yellow oil. This was purified by flash chromatography (2:1 hexanes: EtOAc) to give 7 as a yellow solid (0.91 g, 84%): 1H-NMR (CDCl3) 9.44 (bs, 1H), 7.65-7.68 (m, 1H), 7.32-7.35 (m, 2H), 7.14-7.21 (m, 2H), 3.03 (s, 3H), 1.57 (s, 9H); 13C-NMR (CDCl3) 169.6, 135.7, 127.8, 125.1, 122.3, 120.7, 120.4, 114.9, 111.8, 56.3, 35.2, 27.9; IR (KBr) 3444, 3167, 2945, 1587, 1536, 1446, 1123, 1011 cm-1; UV (95% EtOH) deltamax 296 nm.; MS m/z 230 (M+), 215, 144, 116, 89, 72 (100%). An analytical sample was obtained via iterative recrystallizations from CH2Cl2/hexanes: mp 220-222 C. Anal. Calcd for C14H18N2O: C, 73.01; H, 7.88; N, 12.16. Found: C, 72.80; H, 7.82; N, 12.08.

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

Reference：
Article; Badenock, Jeanese C.; Fraser, Heidi L.; Gribble, Gordon W.; Arkivoc; vol. 2018; 5; (2018); p. 140 – 149;,
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

289483-82-5, 4-Methyl-7-nitro-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10% palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60C, and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50C for 16 hours to give 289 g of the title compound (yield: 84.8%). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395.(HPLC conditions) Mobile phase: CH3CN/H2O/70% HClO4 = 400/600/1 (v/v/v)Flow rate: 1.0 mL/minDetection: UV (282 nm)Column: YMC-Pack Pro C18 250 x 4.6 mm, 289483-82-5

As the paragraph descriping shows that 289483-82-5 is playing an increasingly important role.

Reference：
Patent; Eisai Co., Ltd.; EP1666463; (2006); 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

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

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

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

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