Category: 676273-39-5

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

676273-39-5, Preparation of compound 69c: N’-hydroxy-3-iodo-l-tosyl-l/7-indole-5- carboximidamideTo a suspension of 3-iodo-l-tosyl-l//-indole-5-carbonitrile (1 g, 2.37 mmol) in EtOH (10 mL) was added Et3N (1.65 mL, 11.87 mmol) followed by NH2OH.HCl (410 mg, 5.93 mmol) and the reaction was stirred for 48 h at RT. The solvent was removed in vacuo and the residue was treated with H20 (10 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (25 mL). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The residue was further triturated with n-pentane to give N’-hydroxy-3-iodo-l-tosyl-l//-indole-5- carboximidamide (950 mg, 88.7%o) as an off brown solid. MS (ESI, pos. ion) m/z: 455.8; .H NMR (400MHz, CDC13): delta 7.99 (d, J=8.8Hz, 1H), 7.84-7.73 (m, 4H), 7.68 (d, J=8.4Hz, 1H), 7.63-7.61 (m, 1H), 7.31-7.24 (m, 1H), 4.92 (brs, 2H), 3.14-3.09 (m, 1H), 2.36 (s, 3H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

Reference：
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

676273-39-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

Compound 15 (0.682 g), [2-(trifluoromethyl)-3-thienyl] boronic acid (0.38 g) and 2N solution of Na2CO3 (0.514 g, 2.4ml) were taken in n-Butanol (5ml) in a RB flask. Resulting mixture was de- gassed for 10 min. To this, was added PdCl2(PPh3)2 (0.057 g) and again degassed for 5 min. Resulting reaction mixture was stirred and heated at 110C for 2 hrs under nitrogen atmos- phere. Reaction completion was monitored by TLC. After completion of reaction it was cooled to RT. Filtered the reaction through celite bed and washed with ethyl acetate. Filtrate was washed with water and brine. Organic layer was dried over Na2SO4 and evaporated completely. Crude compound was purified by flash column chromatography. Pure compound was eluted with 10- 25% ethyl acetate in heptane. Evaporated solvent under vacuum. It was concentrated under vacuum to afford 0.25 g (34.70%) of the desired product 18. 1H NMR (300 MHz, DMSO-d6) delta 8.20 (d, J = 8.7 Hz, 1H), 8.11 (d, J = 4.9 Hz, 2H), 8.05- 7.95 (m, 3H), 7.84 (dd, J = 8.7, 1.4 Hz, 1H), 7.51 (dd, J = 5.1, 1.4 Hz, 1H), 7.44 (d, J = 8.2 Hz, 2H), 2.34 (s, 3H).

As the paragraph descriping shows that 676273-39-5 is playing an increasingly important role.

Reference：
Patent; BASF SE; POONOTH, Manojkumar; RHEINHEIMER, Joachim; RATH, Rakesh; ROSENBAUM, Claudia; WIEBE, Christine; BRAHM, Lutz; RUDOLF, Georg Christoph; KHANNA, Smriti; HADEN, Egon; ROEHL, Franz; SIEPE, Isabella; KREMZOW-GRAW, Doris; SCHIFFER, Helmut; (199 pag.)WO2018/210659; (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

676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

676273-39-5, Compound 15 (10 g), Thiophene boronic acid and K2CO3 were taken in Dioxane (120 ml): Wa- ter(15ml) mixture in a two neck RB flask equipped with Nitrogen balloon and reflux condenser. Reaction mass was degassed for 20 min. Palladium catalyst was added and reaction mass was again degassed for 3 min. Reaction mixture was refluxed at 110C for 2 hrs under Nitrogen. Re- action progress was monitor by TLC. After completion of the reaction, the mixture was filtered through a bed of celite. Filtrate was diluted with ethyl acetate. Ethyl acetate layer was washed with water and brine and concentrated. Crude material was taken in 80 ml methanol and stirred for 45 min at RT. Solid obtained is filtered and wash with cold methanol to get 8.4 g white solid product. (0863) 1H NMR (300 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.40 (s, 1H), 8.22- 8.08 (m, 2H), 7.98 (d, J = 8.3 Hz, 2H), 7.82 (d, J = 8.7 Hz, 1H), 7.70 (d, J = 1.8 Hz, 2H), 7.41 (d, J = 8.2 Hz, 2H), 2.31 (s, 3H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BASF SE; POONOTH, Manojkumar; RHEINHEIMER, Joachim; RATH, Rakesh; ROSENBAUM, Claudia; WIEBE, Christine; BRAHM, Lutz; RUDOLF, Georg Christoph; KHANNA, Smriti; HADEN, Egon; ROEHL, Franz; SIEPE, Isabella; KREMZOW-GRAW, Doris; SCHIFFER, Helmut; (199 pag.)WO2018/210659; (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

676273-39-5,676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3 Synthesis of 3-(4-hydroxybut-1-inyl)-1-tosyl-1H-indole-5-carbonitrile (IV) 3-iodo-1-tosyl-1H-indole-5-carbonitrile (V) (12.5 g, 28.3 mmol), PdCl2 (150 mg, 0.85 mmol), PPh3 (668 mg, 2.55 mmol) and CuI (162 mg, 0.85 mmol) are suspended in a mixture of triethylamine (65 mL) and DMF (60 mL) under inert atmosphere. The mixture is heated to the temperature of 30 C., then treated with a solution (10 mL) obtained by dissolving 3-butyn-1-ol (2.7 mL, 30.0 mmol) in DMF added by slow dripping. At the end of the addition the reaction mixture is left to stand at ambient temperature and maintained under stirring overnight. The mixture is then diluted with ethyl acetate (200 mL) and treated with a solution of 1M HCl until markedly acid. The phases are separated and the organic phase is washed sequentially with a saturated solution of NaHCO3 with the addition of a 33% solution of NH4OH, an 0.1M solution of Na2S2O3 and a saturated solution of NaCl. The organic phase is dried on Na2SO4, filtered, and concentrated at low pressure. Crude product (IV) is obtained as a solid (11 g), which is not purified but used “as is” in the subsequent reaction.A portion of the crude product is purified by flash chromatography (petroleum ether/AcOEt 50/50) to obtain chemically pure product ( IV) as a white solid. [0065] 1H-NMR (400 MHz, CDCl3), delta: 7.97 (1H, d, J=8.4 Hz); 7.89 (1H, s); 7.71-7.68 (3H, m); 7.50 (1H, d, J=8.8 Hz); 7.20 (1H, d, J=8.4 Hz); 3.78 (2H, m); 3.65 (1H, bs); 2.67 (2H, t, J=6.4 Hz); 2.29 (3H, s).

676273-39-5 3-Iodo-1-tosyl-1H-indole-5-carbonitrile 21955913, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; DIPHARMA FRANCIS S.R.L.; TADDEI, Maurizio; GIANNOTTI, Luca; ATTOLINO, Emanuele; ALLEGRINI, Pietro; US2014/275542; (2014); 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.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

676273-39-5, Example 44 Preparation of QR-0311[00400] Compound QR-031 1 was prepared by reactions depicted in Scheme 50 below.[00401] The following General Procedure H was used. General Procedure H[00402] Arylbromide or aryliodide (1 mmol). boric acid ( 1.2 mmol) andPd(OAc)2 (0.05 mmol) in DMF (5 niL) were stirred under argon at 60-90 0C for 5-16 h. The mixture was then cooled to room temperature, ethyl acetate (50 mL) was added and the mixture washed with brine 3 times (50 mL). The organic layer wasdried with MgSO4 and concentrated. The residue was purified by flash columnchromatography.100403] General Procedure H was used to yield 259 (63% yield). 1H NMR(CDCl3): 2.38 (s, 3H). 7.30 (d, 2H. J=8.4). 7.37-7.41 (m, 2H), 7.55 (s, I H), 7.64 (d.1 H. J=8.6), 7.82-8-7.86 (m, 4H), 7.96 (s. 1 H), 8.14 (d. 1 H, .1=8.6). 8.31 (s, 1 H).

676273-39-5 3-Iodo-1-tosyl-1H-indole-5-carbonitrile 21955913, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; QUEEN’S UNIVERSITY AT KINGSTON; WO2008/58402; (2008); 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

676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

676273-39-5, 3-Iodo-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (5.0 g, 11.8 mMol) was added to a solution of bis(tributyltin) (6.27 mL, 12.4 mMol) in DMF (50 mL). Triphenyl phosphine (310 mg, 0.10 mMol) and palladium(II)acetate (133 mg, 0.59 mMol) were added and the reaction was heated to 60 C. for 40 min. The reaction was cooled in a water bath, then poured into brine (500 mL), and extracted with ethyl acetate (3×50 mL). The organic phase was dried with magnesium sulfate and the solvent was removed in vacuo. The reaction was purified by chromatography on silica gel with hexanes to remove tin byproducts followed by elution with ethyl acetate/hexanes (8%) to give the product as an off-white solid (5.67 g, 82%). 1H NMR (400 MHz, CDCl3) delta 8.02 (1H, d, J=8.6 Hz), 7.75 (3H, m), 7.52 (1H, dd, J=8.6, 1.5 Hz), 7.49 (1H, s), 7.24 (2H, m), 2.35 (3H, s), 1.05-1.82 (18H, m), 0.89 (9H, m); MS m/e 587.3 (M+H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Denhart, Derek John; Ditta, Jonathan L.; King, Dalton; Macor, John E.; Marcin, Lawrence R.; Mattson, Ronald J.; Meng, Zhaoxing; US2004/63768; (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