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;,
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

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

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

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

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

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

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20265-35-4, name is 2-Methoxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6N2O3

Method 4 Synthesis of 7-methoxy-1H-pyrrolo[2,3-c]pyridine (Intermediate 5) A solution of R-4 (500 mg, 3.24 mmol) in anhydrous THF (20 mL) is cooled to -78° C. and vinylmagnesium bromide (9.73 mL of a 1 M solution in THF, 9.73 mmol) added. The reaction is stirred at -20° C. for 6 h then quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase is concentrated in vacuo and the crude material purified by flash chromatography (SiO2, 2percent to 10percent MeOH in DCM) to give the title intermediate I-5 (100 mg) m/z 148.9 [M+H].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 20265-35-4, 2-Methoxy-3-nitropyridine.

Reference:
Patent; BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M.; US2013/196967; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86604-79-7, 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 86604-79-7, name is 2,3,5-Trimethyl-4-nitropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows.

The 2,3,5-trimethyl-4-nitropyridine1-oxide (13.4 g, 73.6 mmol) obtained in the step (11c) was added to acetyl chloride (80 ml, 1,125 mmol) at -30 C. in a nitrogen atmosphere. The mixture was stirred at -30 C. to room temperature for 4 hours and 20 minutes. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=10/1) to obtain fractions containing a pure product of the title compound and fractions containing a crude product of the title compound. The fractions containing a crude product of the title compound was concentrated. The residue was suspended in ethyl acetate and the resulting precipitate was collected by filtration, washed with ethyl acetate and diethyl ether to obtain the title compound (Lot A, 1.58 g) as a white solid. The filtrate was concentrated. The residue was dissolved in chloroform and washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was suspended in diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether to obtain the title compound (Lot B, 2.69 g) as a pale brown solid. The fractions containing a pure product of the title compound were concentrated. The residue was dissolved in chloroform, washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the title compound (Lot C, 6.56 g) as a pale white solid. The yield of the obtained title compounds of 3 lots was 85.7% in total. Lot A: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot B: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot C: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s).

According to the analysis of related databases, 86604-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65515-32-4 ,Some common heterocyclic compound, 65515-32-4, molecular formula is C8H8ClNO3, 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.

To a solution of 6-Chloro-2-methoxy-nicotinic acid methyl ester (18.5.0 g, 0.092 mol) in 50 mL of NMP was added p-methoxybenzylamine (19.0 g, 0.14 mol) and triethylamine (10.Og, 0.1 mol). The mixture was heated to 70 0C for 4 h, cooled and diluted with water and extracted with ethyl acetate, washed with water, brine, dried with sodium sulfate, and evaporated to get an oil which was precipitated with ethylacetate/hexane mixture (1 :1). This was then filtered and dried to yield 15 g (60 %) of the target compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-32-4, its application will become more common.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem