Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 13959-02-9, 3-Bromoisonicotinic acid, 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, 13959-02-9, blongs to pyridine-derivatives compound. Quality Control of 3-Bromoisonicotinic acid

General procedure: To a solution of Intermediate 7 (110 mg, 0.37 mmol), 3-methoxybenzene-1,2- diamine (50 mg, 0.34 mmol) and DIPEA (0.2 mL, 1 mmol) in DMF (2 mL) was added HATU (160 mg, 0.41 mmol). The reaction mixture was stirred at r.t. for 48 h, then partitioned between DCM and water. The organic phase was separated, then dried and concentrated in vacuo. The crude residue was purified by flash column chromatography (0-100% EtOAc/hexanes) to give the title compound (28.7 mg, 20%) as a white solid. LCMS (Method 5): [M+H]+ m/z 415, RT 1.31 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; FOULKES, Gregory; FROST, James Richard; HORSLEY, Helen Tracey; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; REUBERSON, James Thomas; SCHULZE, Monika-Sarah Elisabeth Dorothea; TAYLOR, Richard David; YAU, Wei Tsung; ZHU, Zhaoning; (246 pag.)WO2019/138017; (2019); A1;,
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Synthetic Route of 6188-23-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6188-23-4 as follows.

To a solution of 6-bromoimidazo[1,2-a]pyridine (318 mg, 1.61 mmol) in 1,4-dioxane (15 mL) were added N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide (600 mg, 1.69 mmol), KOAc (316 mg, 3.22 mmol), H2O (3 mL) and Pd(dppf)Cl2.CH2Cl2 (131 mg, 0.161 mmol). The reaction was heated to 85 C. and stirred further for 5 hours under N2 atmosphere, then cooled to rt, and concentrated in vacuo. The residue was dissolved in DCM (200 mL) and the resulted mixture was filtered through a CELITE. The filtrate was washed with H2O (100 mL) and brine (100 mL). The combined aqueous layers were extracted with DCM (50 mL*3). The combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v)=65/1) to give the title compound as a yellowish solid (342 mg, 62%). MS (ESI, pos. ion) m/z: 345.0 [M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.91 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.68-7.61 (m, 2H), 7.54 (dd, J=1.8, 9.6 Hz, 1H), 3.98 (s, 3H), 2.82-2.74 (m, 1H), 1.00-0.89 (m, 4H).

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; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 866755-20-6, 2,6-Dichloro-3-bromopyridine, 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, SDS of cas: 866755-20-6, blongs to pyridine-derivatives compound. SDS of cas: 866755-20-6

Fresh cut sodium (0.101 g 4.41 mmol) was added to EtOH (50 mL) . The resulting mixture was stirred at rt. After the solid dissolved 3-bromo-2 6-dichloropyridine (1 g 4.41 mmol) was added. The resulting mixture was stirred at 70 overnight. After LCMS analysis showed the starting material was disappeared. The solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with H2O (20 mL) and brine (20 mL) . The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica column chromatography (PE/EA 20/1) to yield a white solid of a mixture of 3-bromo-2-chloro-6-ethoxypyridine 3-bromo-2 6-diethoxypyridine and 3-bromo-6-chloro-2-ethoxypyridine (930 mg 3.85 mmol 87yield) 1HNMR(400 MHz CD3OD) delta 7.85 (d J 1.2 Hz 1H) 6.88 (d J 8.0 Hz 1H) 4.42-4.36 (m 2H) 1.39 (t J 7.2 Hz 3H) ES-LCMS m/z 235.9 237.9 (M+H)

The synthetic route of 866755-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89284-61-7 , The common heterocyclic compound, 89284-61-7, name is 4-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Intermediate 35 (0.10 g, 0.383 mmol) was dissolved in anhydrous THF (3.99 mL), and 60% wt. in mineral oil) (0.034 g, 0.842 mmol) was added in one portion at 0 C. After 30 4-chloronicotinonitrile (0.133 g, 0.957 mmol) and was added in one portion, and the on mixture was allowed to reach rt overnight (16 h). Afterwards, the reaction mixture was hed with NH4Cl (2 mL), diluted with EtOAc (50 mL), washed with water (2×10 mL), (1×20 mL), dried (Na2SO4), filtered, concentrated, and purified by normal phasematography to give Example 44A (138 mg, 99%). MS (ESI) m/z: 364.1 (M+H)+. Example 44B. Preparation of 4-((aR)-6-aminospiro[3.3]heptan-2- y)nicotinamide NH2

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
Pyridine – Wikipedia,
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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem