Category: pyridine-derivatives

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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4FNO

A mixture of [3-(6-morpholin-4-yl-9-piperidin-4-yl-9H-purin-2-yl)phenyl]methanol (30 mg, 0.076 mmol), NaCNBH3 (25 mg, 0.40 mmol), zinc chloride (20 mg, 0.183 mmol) and 6-fluoronicotinicaldehyde (14 mg, 0.11 mmol) in methanol is stirred for 24 hours at room temperature. The mixture is then filtered, dissolved in DMSO (1 mL) and purified by chromatography by HPLC to give 9 mg (24% yield) of the title product.

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, 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; Wyeth; US2008/233127; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 117007-52-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

Step 3: tert-butyl 3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (49-4); A magnetically stirred suspension of 1.20 g (4.90 mmol) of 3-iodo-1H-pyrazolo[3,4-b]pyridine (49-3) in 35 mL of anhydrous acetonitrile under a nitrogen atmosphere was treated with 720 muL (5.15 mmol) of triethylamine, followed by 599 mg (4.90 mmol) of 4-dimethylaminopyridine. The resulting solution was treated approximately 2 minutes later with a solution of 1.29 g (5.88 mmol) of BOC anhydride in 5 mL of anhydrous acetonitrile, and the resulting solution stirred at room temperature for 72 hours. The crude reaction mixture was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine, and dried in vacuo (anhydrous MgSO4). The dried extract was filtered, and the filtrate concentrated in vacuo to give 2 g of the crude solid product. The product was purified by flash chromatography over silica gel with 20:1 hexanes/EtoAc (crude material dissolved in chloroform, impregnated on silica, and the silica applied to the top of the column) to give the desired product as a white solid. M+=245 (M-100, loss of BOC). 1H NMR (CDCl3): 1.73(s, 9H), 7.36(dq, 1H), 7.84(dd,1H), 7.78(dd,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16063-69-7 , The common heterocyclic compound, 16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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.

Samples of 0.500 g (2.74 mmol) 2,4,6-trichloropyridine, 0.487 g (3.29 mmol) trans-2-phenylvinylboronic acid, 0.057 g (0.082 mmol) Pd(Cl2)(PPh3)2, and 1.17 g (5.48 mmol) K3PO4 were combined in 20 mL THF. To this heterogeneous mixture, 2.5 mL of H2O were added. The resulting solution was heated at reflux for 20 h. After being cooled to room temperature, the resulting residue was extracted from water with three times with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and the solvent removed with a rotary evaporator. The product was purified by column chromatography (5-10% EtOAc in hexanes) to provide pure 14 (0.323 g, 47% yield). 1H NMR (500 MHz, CDCl3) delta 7.01 (d, J=16.08 Hz, 1H), 7.19 (s, 1H), 7.25 (s, 1H), 7.34 (t, J=7.07 Hz, 1H), 7.40 (t, J=7.50 Hz, 2H), 7.57 (d, J=7.29 Hz, 2H), 7.70 (d, J=15.87 Hz, 1H). 13C NMR (500 MHz, CDCl3) delta 120.6, 121.9, 125.1, 127.4, 128.8, 129.0, 135.6, 135.7, 145.8, 151.7, 157.1. HRMS (ESI+) m/z calcd for C13H10NCl2+ 250.0190. found 250.0188. mp 36-38 C. (recryst. from EtOAc/hexanes).

The synthetic route of 16063-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; DUKE UNIVERSITY; Katzenelienbogen, John; McDonneli, Donald; Norris, John D,; Parent, Alexander; Pollock, Julie; Gunther, Jillian; Carlson, Kathryn E.; Martin, Teresa; (196 pag.)US2016/229811; (2016); A1;,
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

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

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

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. 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

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

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