Pyridine-derivatives

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1080026-94-3, name is Ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate, the common compound, a new synthetic route is introduced below. COA of Formula: C10H13NO2S

615 mg (987 mumol, 50% purity) 5-tert.-butyl-2-ethyl 6,7-dihydro-4H-thieno[3,2-c]pyridine-2,5-dicarboxylate are dissolved in 4 ml of a mixture of TFA and DCM (v/v 1:1) and stirred for 30 minutes at RT. The reaction mixture is neutralised by the addition of TEA and evaporated down i. vac.The crude product thus obtained is dissolved in 4 ml formic acid and combined with 0.5 ml (6.7 mmol) formalin solution (37% in water). The reaction mixture is stirred for 16 hours at 70 C. After cooling to RT the mixture is made basic with 50% aqueous sodium hydroxide solution and saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase is washed three times with water, dried on sodium sulphate, filtered and evaporated down i. vac. The residue is purified by RP-HPLC.Rt value: 0.90 min (Method B)C11H15NO2S×CF3CO2H (225.31)Mass spectrum: (M+H)+=226

The synthetic route of 1080026-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/99664; (2010); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 89284-61-7, name is 4-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. Safety of 4-Chloronicotinonitrile

A solution of 4-chloronicotinonitrile (1.00 g, 7.22 mmol), 4- methoxybenzylamine (1.03 ml, 7.94 mmol) and potassium carbonate (1.20 g, 8.66 mmol) in propan-2-ol (20 mL) was heated under reflux for 18 hours. The solvent was concentrated in vacuo and the residue partitioned between EtOAc (150 mL) and water (50 mL). The organic phase was dried (Na2SO4), filtered and evaporated to give a brown oil. The oil was pre- adsorbed onto H-MN and purified by flash column chromatography (Si- PPC, cyclohexane: EtOAc, gradient 80:20 to 0:100) to provide the title compound as a white solid (1.61 g, 93%). IH NMR (CDCl3, 300 MHz) 8.46 (d, J = 0.7 Hz, IH), 8.30 (dd, J = 6.1 Hz, 0.7 Hz, IH), 7.24 (dd, J = 8.6 Hz, 2.1 Hz, 2H), 6.92 (dd, J = 8.6 Hz, 2.1 Hz, 2H), 6.55 (d, J = 6.1 Hz, IH), 5.35 (br t, IH), 4.40 (d, J = 5.6 Hz, 2H), 3.82 (s, 3H).

The synthetic route of 89284-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; WO2008/67481; (2008); A1;,
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Electric Literature of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
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Adding a certain compound to certain chemical reactions, such as: 60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 60832-72-6, blongs to pyridine-derivatives compound. Recommanded Product: 60832-72-6

To a stirred suspension of [1 ,3]oxazolo[4,5-o]pyridin-2(3H)-one (1-51) (34 g, 0.25 mol) in MeCN (0.35 L) was added NBS (47.6 g, 0.275 mol) in a portionwise manner at 0 C. After addition, the reaction mixture was stirred at room temperature for 3 h. TLC (EtOAc/hexane = 1 :1) indicated the reaction was complete. The precipitate was filtered, washed with cold MeCN (150 ml_) and dried under vacuum to yleld 6-bromo[1 ,3]oxazolo[4,5-o]pyridin-2(3H)-one (I-52) (45 g, 84%) as a yellow solid, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60832-72-6, its application will become more common.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
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Related Products of 143468-13-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 143468-13-7, name is 6-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 6 (1mmol) and 4-nitrophenylchloroformate (1.6mmol) in toluene (18mL, for 7g, h, k, q, r, 8) or CH2Cl2 (18ml for 7j) containing NaOH (3mmol) and a catalytic amount of Bu4NBr (0.05mmol) was heated (40-100C) for 2-7h under a stream of nitrogen. Ethyl acetate was added and the organic phase was washed with water, dried over Na2SO4 and filtered. Following this procedure compounds 7g, h, j, k, q, r, 8 were prepared.

According to the analysis of related databases, 143468-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Merlini, Lucio; Giannini, Giuseppe; Vesci, Loredana; Milazzo, Ferdinando M.; Carenini, Nives; Perego, Paola; Penco, Sergio; Artali, Roberto; Zunino, Franco; Pisano, Claudio; Dallavalle, Sabrina; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1089 – 1103;,
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Application of 103-74-2, Adding some certain compound to certain chemical reactions, such as: 103-74-2, name is 2-(2-Hydroxyethyl)pyridine,molecular formula is C7H9NO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 103-74-2.

A mixture of 107.5 mg (0.2 mmol) of acid, 45.8 mg (0.22 mmol) of DCC and 6.9 mg (0.05 mmol) of HOBt in 50 ml of DCM is cooled in a bath of ice-cold water. 75.4 mg (0.6 mmol) of the required alcohol are added thereto. The mixture is allowed to warm to room temperature and is stirred for 20 hours. After washing with water, drying (NagSC^) and evaporating, a pasty product is obtained, which is purified by chromatography (SiOa, 1/1 EtOAc/heptane) to give 60 mg (46%) of a pasty product.

According to the analysis of related databases, 103-74-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; WO2006/10423; (2006); A2;,
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Pyridine | C5H5N – PubChem

Reference of 78686-83-6 ,Some common heterocyclic compound, 78686-83-6, molecular formula is C7H5ClINO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 2 Methyl 2-chloro-5-ethynylpyridine-3-carboxylate Under an atmosphere of inert gas, 20 g (67.23 mmol) of methyl 2-chloro-5-iodopyridine-3-carboxylate are stirred together with 200 ml of triethylamine, 8 g (81.45 mmol) of trimethylsilylacetylene, 3 g (15.71 mmol) of CuI, 4.3 g (16.41 mmol) of triphenylphosphine and 3.04 g (4.33 mol) of Pd(PPh3)2Cl2 at 50 C. for 12 hours. The reaction mixture is then stirred with 40 ml of methanol and 4 g (33.61 mmol) of potassium carbonate at room temperature for a further 2 hours. The solids are filtered off and the filtrate is diluted with water and extracted three times with ethyl acetate. The combined organic extracts are washed three times with saturated aqueous NaCl solution and then dried over sodium sulphate and subsequently filtered. The filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel using an ethyl acetate/cyclohexane gradient. Yield: 7.5 g (57% of theory) as a brown solid. 1H NMR (300 MHz, CDCl3, 25 C.): 8.70-8.71 (1H, d), 8.33-8.34 (1H, d), 4.68 (1H, s), 3.89 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-83-6, its application will become more common.

Reference:
Patent; BAYER ANIMAL HEALTH GMBH; SCHWARZ, Hans-Georg; HALLENBACH, Werner; GOeRGENS, Ulrich; ILG, Kerstin; TURBERG, Andreas; (46 pag.)US2017/112129; (2017); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 100137-47-1, name is 4-Aminopicolinamide, molecular formula is C6H7N3O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H7N3O

To a solution of 4-aminopyridine-2-carboxamide (2.90 g, 21.2 mmol) and DIEA (7.19 g, 55.7 mmol) in NMP (27 mL) at 0 C was added dropwise a solution of 2-fluoro-4-(trifluoromethoxy)benzoyl chloride (5.40 g, 22.3 mmol) in dichloromethane (27 mL). The reaction mixture was removed from the ice bath and stirred at room temperature for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The crude material was triturated with a mixture of hexanes/dichloromethane and the solid was collected by vacuum filtration to obtain 4-[[2-fluoro-4-(trifluoromethoxy)benzoyl]amino]pyridine-2-carboxamide (650 mg, 9%). ESI-MS m/z calc. 343.05, found 344.1 (M+l)+; retention time (Method B): 1.65 minutes(3 minute run). NMR (400 MHz, DMSO-d6) delta 1 1.09 (s, 1H), 8.56 (d, J = 5.6 Hz, 1H), 8.36 (d, J = 2.2 Hz, 1H), 8.1 1 (d, J = 2.7 Hz, 1H), 7.95 – 7.80 (m, 2H), 7.74 – 7.54 (m, 2H), 7.50 – 7.32 (m, 1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 100137-47-1.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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Related Products of 109-04-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, molecular weight is 157.996, as common compound, the synthetic route is as follows.

2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90 C overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.

Statistics shows that 109-04-6 is playing an increasingly important role. we look forward to future research findings about 2-Bromopyridine.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2007/130743; (2007); A2;,
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Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

To a solution of sulfurisocyanatidic chloride (37 mg, 0.26 mmol) in DCM (2 mL) in an ice-water bath was added a solution of Intermediate GW-13.2 (100 mg, 0.26 mmol) and TEA (0.11 mL, 0.79 mmol) in DCM (2 mL) and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (48 mg, 0.39 mmol) in DCM (2 mL) was added, followed by TEA (0.15 mL, 1.1 mmol), the bath was removed and the stirring was continued at rt for 2 h. The reaction mixture was concentrated, the residue was redissolved in DMF and purified by preparative HPLC to afford the title compound (31.4 mg). LC-MS retention time = 3.06 min; m/z = 554.16 [M+Na]+. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 mupiiota particles; Mobile Phase A: 10% MeOH- 90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

With the rapid development of chemical substances, we look forward to future research findings about 10592-27-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
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