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. 136818-50-3, name is 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. name: 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid

To the stirred solution of lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid (5, 2.5 g, 15.4 mmol) and Nu,Omicron-dimethylhydroxylamine hydrochloride (6, 1.8 g, 18.5 mmol in DCM (50 mL), was added triethylamine (10.6 mL, 77.1 mmol), HOBt (3.54 g, 23.14 mmol) followed by EDC.HC1 (4.42 g, 23.18 mmol) at 0C and the reaction mixture was stirred at room temperature for 16h. The reaction mixture was cooled to room temperature, filtered through celite and evaporated the filtrate. To the crude, added water (10 mL) and compound was extracted with DCM (30mL). Organic layer was dried over sodium sulfate and evaporated to get crude product. The crude residue was purified by gradient column chromatography using silica gel and eluent 2-4% MeOH in DCM to afford the product as off white solid. (Yield: 82%, 2.6 g). MS (ESI): mass calcd. for CioHnN302, 205.09; m/z found, 206.1 (M+H)+.

The synthetic route of 136818-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.882033-66-1, name is 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4ClFN2, molecular weight is 170.5715, as common compound, the synthetic route is as follows.COA of Formula: C7H4ClFN2

Example 224A mixture of 4-chloro-5-fluoro-lH-pyrrolo [2, 3-b] pyridine (30 mg) , 3-piperidinecarboxamide (45 mg) and N,N-diisopropylethylamine (30 muL) inDMI(0.4mL) was heated in the microwave reactor (2000C, 2 hours) . The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodium hydrogencarbonate (10 mL) . The aqueous phase was extracted with EtOAc(2x 10 mL) and combined organic layers were washed with brine (20 mL) , dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave 1- (5-fluoro-lH-pyrrolo [2, 3-b]pyridin-4-yl) -3- EPO piperidinecarboxamide (5 mgj as a pale brown solid.1H-NMR(DMSO-d) delta : 11.5 (IH, s) , 7.96 (lH,d, J=5.7Hz) , 7.38 (IH, s) , 7.33 (1H,d, J=3.0Hz) , 6.87 (IH, s), 6.49 (IH, d, J=3.0Hz) , 3.82-3.70 (2H,m) ,3.21-3.06 (2H,m), 2.52-2.44 (IH,m) , 1.94-1.52 (4H,m) . ? MS(ESI) :m/z 263(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,882033-66-1, 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5632-81-5, 2-Chloropyridine-3,5-diamine, 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, 5632-81-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

REFERENCE EXAMPLE 18 Synthesis of ethyl 3-[(5-amino-6-chloropyridin-3-yl)amino]-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate To 1.4 g of ethyl 3-chloro-2,4,5-trifluorobenzoyl-acetate were added 1.5 g of acetic anhydride and 1.5 g of triethyl orthoformate, and the mixture was heated under reflux for 2 hours. The solvent was distilled off, and toluene was added to the residue for azeotropic distillation. 3 ml of chloroform was added to the half of the residue, and a solution of 360 mg of 3,5-diamino-2-chloropyridine in 3 ml ethanol was added dropwise to the mixture at room temperature and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off, and the residue was purified by column chromatography to obtain 200 mg of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5632-81-5, its application will become more common.

Reference:
Patent; Wakunaga Pharmaceuticals Co., Ltd.; US5998436; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1945-84-2, 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. 1945-84-2, name is 2-Ethynylpyridine, molecular formula is C7H5N, 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.

General procedure: 3-Amino-2-bromopyridine (1a) (87 mg, 0.5 mmol) or2-bromoaniline (1b) (172 mg, 1.00 mmol), Pd(PPh3)2Cl2(9.0 mg, 13 mmol or 17.5 mg, 25.0 mmol), and(1-Ad)2PBn·HBr (12 mg, 25 mmol or 23.6 mg, 50.0 mmol)were placed into a dry screw-cap Schlenk tube with amagnetic stirring bar, and the vessel was evacuated. Afterflushing the vessel with nitrogen, dry DMSO (1.0 or 1.5 ml),the corresponding alkyne 2a-j (0.6 mmol or 1.2 mmol),and DBU (225 mg, 1.50 mmol or 457 mg, 3.00 mmol)were added. The reaction mixture was stirred at 100Cunder nitrogen for 1 h until the bromide was completelyconsumed (monitored by TLC). After cooling to roomtemperature, KOt-Bu (253 mg, 2.25 mmol or 281 mg,2.50 mmol) and DMSO (0.50 or 1.00 ml) were added to thereaction mixture, and the mixture was stirred at 100Cunder nitrogen for 0.25 h. After cooling to roomtemperature, deionized water or brine (20 ml) was added tothe mixture. The aqueous layer was extracted several timeswith EtOAc or CH2Cl2. The combined organic phases weredried over anhydrous Na2SO4 and after filtration, thesolvents were removed under reduced pressure. The residuewas purified by flash chromatography on silica gel to givethe analytically pure products 3a-j

According to the analysis of related databases, 1945-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lessing, Timo; Mueller, Thomas J. J.; Chemistry of Heterocyclic Compounds; vol. 54; 3; (2018); p. 334 – 338; Khim. Geterotsikl. Soedin.; vol. 54; 3; (2018); p. 334 – 338,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1039416-36-8, 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. 1039416-36-8, name is 6-Chloroimidazolo[1,2-a]pyridin-2-yl-methanol, molecular formula is C8H7ClN2O, 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.

Step (a) 6-chloroimidazo[l,2-a]pyridine-2-carbaldehyde; 6-Chloro-imidazo[l,2-a]pyridine-2-carboxylic acid (0.4 g, 2 mmol) was dissolved in dry THF (10 ml) and 1.0M borane/THF solution (5 ml, 5 mmol) was added, and the mixture heated at reflux for 2h. Mixture was quenched with methanol (2 ml), acidified with 3 drops of concentrated hydrochloric acid and heated at reflux for 15 min. The mixture was then adsorbed on to SCX resin, washed well with methanol and the crude alcohol intermediate eluted with 10% aqueous ammonia in methanol. This intermediate (0.4 g, 2.2 mmol) was mixed with manganese dioxide (2 g, 23 mmol) in dichloromethane (50 ml) and was heated at reflux for 30 min. The inorganics were removed by filtration and the filtrate evaporated to dryness to afford the sub-title compound (0.32 g, 89%). 1H NMR (300 MHz, CDCl3): delta 10.22 (s, IH), 8.33 (s, IH), 8.09 (s, IH), 7.64 (d, IH), 7.27 (dd, IH)

According to the analysis of related databases, 1039416-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84236; (2008); 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. 64188-97-2, name is 3-Aminoisonicotinamide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7N3O

[00155j To a solution of 3-aminopyridine-4-carboxamide (5 g, 36.5 mmol) in THF (100 mL) was added triphosgene (11.9 g, 40.1 mmol) and TEA (7.4 g, 73 mmol). The reaction mixture was refluxed for 2h. The solution was concentrated in vacuo and the residue was triturated in water. The solid was filtered and washed with water and THF. The solid was dried to afford 4.lg (70%) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 11.62 (s, 1H), 11.58 (s, 1H), 8.66 (s, 1H), 8.40 (d, 1H,J= 5.2Hz), 7.80 (d, 1H,J 5.2 Hz).

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, 64188-97-2, 3-Aminoisonicotinamide.

Reference:
Patent; QUANTICEL PHARMACEUTICALS, INC.; BOLOOR, Amogh; KANOUNI, Toufike; STAFFORD, Jeffrey Alan; VEAL, James Marvin; WALLACE, Michael Brennan; (173 pag.)WO2016/44429; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 372-47-4, 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.372-47-4, name is 3-Fluoropyridine, molecular formula is C5H4FN, molecular weight is 97.09, as common compound, the synthetic route is as follows.

a) synthesis of l-(3-Fluoro-pyridin-2-yl)-ethanone (2a)[0205] A solution of BuLi (39.5 ml, 98.7 mmol, 2.5 M in hexane) in 100 ml THF was added to a solution of 3-fluoropyridine (1) (8g, 82.3 mmol) in 20 ml THF of at – 78 C. The reaction mixture was stirred at -78 C for 30 min. Then, N-methyl-N- methoxyacetamide 10.9 ml (106.9 mmol) was added at – 78 C. The reaction mixture was slowly warmed up to room temperature and stirred for 1 hour. The reaction was quenched with ice-cold saturated aqueous ammonium chloride solution. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified via column chromatography (Ethyl acetate: n-Hexane = 1 : 6) and a 1 : 1 mixture of (2a) and (2b) was obtained 4.78 g (yield: 42%).

The chemical industry reduces the impact on the environment during synthesis 372-47-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CRYSTALGENOMICS, INC.; PALKION, INC.; HONG, Yong, Rae; LEE, Mi, Jung; KIM, Jeong, Mi; PARK, Soobong; LEE, Wheeseong; CHOI, Jong-Ryoo; RO, Seonggu; CHO, Joong, Myung; MASAMUNE, Hiroko; ELLIOTT, Gary, T.; WO2011/56725; (2011); 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. 1702-17-6, name is 3,6-Dichloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1702-17-6

EXAMPLE 7 3,6-bis(n-hexylthio)-2-pyridinecarboxylic acid To 300 ml of DMSO was added 84.5 g of powdered NaOH with vigorous stirring followed by the addition of 150 g of n-hexyl mercaptan. The anion of the mercaptan was allowed to form and then 111 g of 3,6-dichloro-2-pyridinecarboxylic acid in 110 ml of DMSO was added through a dropping funnel. the temperature was increased during addition to 135 C. and maintained at that temperature for 21/2 hours. Upon cooling the brown solution was poured into three volumes of water. The resulting solution was acidified with HCl and extracted with 1,1,1-trichloroethane. The organic layer was dried over MgSO4 and the solvent removed on a rotary evaporator. The reaction yielded 155 g (68% yield) of 3,6-bis(n-hexylthio)-2-pyridinecarboxylic acid as a dark oil which solidified on standing; m.p. 40-42 C.

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, 1702-17-6, 3,6-Dichloropicolinic acid.

Reference:
Patent; The Dow Chemical Company; US4371537; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60832-72-6, 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. 60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4N2O2, 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.

Example 2 DMF was added to a 10L three-neck round bottom flask (2000mL) with reflux condenser on each neck. Oxazole [4,5-b]pyridine-2(3H)-one (497g) was added with mechanical stirring until it was dissolved. N- chlorosuccinimide (608g) was dissolved in DMF (2500mL). Transferred to a pressure-equalizing dropping funnel, N-chlorosuccinimide was slowly added dropwise to the reaction flask, the reaction temperature is controlled not to exceed 40C (cooling with ice-water if necessary). Afterwhich, the ice bath was removed, then stirred at room temperature overnight. The reaction was monitored by TLC and GC. After completion of the reaction, 4000mL water was slowly added under cooling with ice water. The reaction mixture was stirred for 30 minutes and filtered. The filter cake was washed twice with water and dried under vacuum to give crude 530g. The crude product was recrystallized from ethyl acetate and methylene chloride to give pure product 6-chlorooxazole[4,5-b]pyridine-2(3H)-one (505g), yield 81%, purity 99.1% (GC) . Melting point 184C ~ 187C (literature 183C ~ 186C).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one.

Reference:
Patent; Dingtao YOUBANG Chemical Co., Ltd.; Fan, Hongli; Han, Meng; Zhao, Jingtao; Lai, Xinsheng; (5 pag.)CN103755627; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 66572-56-3, 2-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, Formula: C6H4BrNO2, blongs to pyridine-derivatives compound. Formula: C6H4BrNO2

a) 2-Bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide To a stirred solution of 455 mg (2.25 mmol) 2-bromo-isonicotinic acid in 8 ml THF were added 914 mg (2.40 mmol) HATU and 0.50 ml (4.51 mmol) N-methylmorpholine and stirring continued at 50 C. for 16 h. 200 mg (0.75 mmol) 7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine was then added and stirring continued at 60 C. for 4 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (methanol/dichloromethane) afforded 208 mg (62%) 2-bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 452 (M{81Br}+H+, 95), 450 (M{79Br}+H+, 100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66572-56-3, 2-Bromoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Norcross, Roger David; US2005/65151; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem