Category: pyridine-derivatives

Synthetic Route of 53547-60-7, Adding some certain compound to certain chemical reactions, such as: 53547-60-7, name is 4-Methylpyridine-2-carbaldehyde,molecular formula is C7H7NO, 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 53547-60-7.

Example 224 4-Amino-6-chloro-2-(1-(4-methyl-2-pyridyl)pentyl)thio-pyrimidine (Cpd #224) A solution of n-butyllithium (6.71 ml, 10.74 mmol, 1.3 equiv., 1.6 M in hexanes) in 60 ml of ether at 0-5 C., is treated dropwise with 4-methyl-2-pyridinecarboxaldehyde (1.0 g, 8.26 mmol, 1.0 equiv.) in 40 ml of ether over a period of 10 min. After 30 min the contents are poured into 45 ml of 3 N HCl containing 60 ml of crushed ice. The cold mixture is warmed to room temperature, stirred for 20 min, basified with 15 ml of 29% aqueous ammonium hydroxide and extracted once with ethylacetate. The organic layer is dried over anhydrous Na2 SO4 and concentrated at reduced pressure. Chromatography with 150 g of silica gel packed and eluted with ethylacetate-hexane (1:2) provided 0.364 g (24%) of 2-(1-hydroxy)pentyl-4-methylpyridine. TLC (silica gel GF): Rf =0.18 ethylacetate-hexane (1:2). 1 H NMR (CDCl3,TMS): delta 8.24 (d, 1H, J=5.05 Hz), 6.92 (s, 1H), 6.87 (d, 1H, J=4.93 Hz), 4.55 (m, 1H), 4.01 (brs, 1H), 2.23 (s, 3H), 1.75-1.45 (m, 2H), 1.34-1.12 (m, 2H), 1.34-1.12 (m, 4H), 0.76 (t, 3H, J=7.19 Hz).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 53547-60-7, 4-Methylpyridine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia & Upjohn Company; US6043248; (2000); A;,
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. 1289197-78-9, name is 2-Bromo-4-chloronicotinaldehyde, the common compound, a new synthetic route is introduced below. COA of Formula: C6H3BrClNO

Example 147a 4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)nicotinaldehyde 147a A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (50 mL), 2-bromo-4-chloronicotin-aldehyde 103a (1.4 g, 6.4 mmol), 3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1(2H)-one 112d (0.6 g, 3.2 mmol), Pd2(dba)3 (293 mg, 0.32 mmol), XantPhos (370 mg, 0.64 mmol), and potassium acetate (627 mg, 6.4 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 80 C overnight. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with CH2Cl2/CH3OH (20:1, V/V) to afford 147a (528 mg, 50%) as a yellow solid. MS: [M+H]+ 330. 1H NMR (500 MHz, CDCl3) delta 10.09 (s, 1H), 8.37 (d, J=5.5, 1H), 7.16 (d, J=5.5, 1H), 6.25 (s, 1H), 4.29-4.32 (m, 2H), 3.83-3.86 (m, 2H), 2.96-2.99 (m, 2H), 2.77-2.78 (m, 2H), 2.00-2.07 (m, 2H), 1.83-1.85 (m, 2H)

The synthetic route of 1289197-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1187449-01-9, Adding some certain compound to certain chemical reactions, such as: 1187449-01-9, name is 4-Bromo-5-chloropyridin-2-amine,molecular formula is C5H4BrClN2, 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 1187449-01-9.

3-Mercaptopropionic acid 2-ethylhexyl ester (0.47 mL, 4.3 mmol) and Hunig’s base (1.4 mL, 7.9 mmol) were added to a mixture of 3-chloro-4-iodo-2-methylpyridine (1.0 g, 3.945 mmol), Pd(OAc)2 (0.044 g, 0.20 mmol) and xantphos (0.230 g, 0.40 mmol) in dioxane (13 mL, 4.0 mmol) under Ar gas. The reaction was heated to 100 C under Argon for 18 hours. The reaction was diluted in EtOAc (60 mL) and filtered through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel (5-60% EtOAc in hexanes) to provide methyl 3-((3-chloro-2-methylpyridin-4-yl)thio)propanoate (962 mg, 3.9 mmol, 99 % yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1187449-01-9, 4-Bromo-5-chloropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BOYS, Mark Laurence; CHICARELLI, Mark Joseph; COOK, Adam; ELSAYED, Mohamed S. A.; FELL, Jay B.; FISCHER, John P.; HINKLIN, Ronald Jay; MCNULTY, Oren T.; MEJIA, Macedonio J.; RODRIGUEZ, Martha E.; WONG, Christina E.; (259 pag.)WO2020/81848; (2020); 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. 6937-03-7, name is Methyl 2-aminoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6937-03-7

To a solution of Methyl 2-aminopyridine-4-carboxylate (10.0 g, 66 mmol, 1.0 equiv) in EtOH (150 ml) was added NaHCO3 (11.1 g, 132 mmol, 2.0 equiv) followed by chloroacetaldehyde (50% by weight in water, 13.0 ml, 99 mmol, 1.5 equiv). The mixture was refluxed for 2 h. Solvents were removed under reduced pressure and the crude mixture was partitioned between water and EtOAc. The resulting precipitate was washed with Et2O and recrystallised from MeOH/Et2O to afford 8.4 g of product. 1 H NMR (400 MHz, DMSO-d6): 8.66 (1 H, d), 8.16 (2H, s), 7.80 (1 H, s), 7.33 (1 H, d), 3.90 (3H, s). MS: [M+H]+ 177.

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, 6937-03-7, Methyl 2-aminoisonicotinate.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2009/47506; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 66171-50-4, 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 66171-50-4, name is Methyl 6-hydroxynicotinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 25 mL Teflon-sealed flask was charged with the corresponding 2-pyridone 1 (0.5 mmol), diaryliodonium salt 2 (0.75 mmol, 1.5 equiv),and Cs2CO3 (0.75 mmol, 1.5 equiv) under an air atmosphere. DCE (5mL) was added to the flask. Then, the reaction vessel was sealed witha Teflon cap. The reaction mixture was stirred at 120 C until the2-pyridone 1 was consumed completely (monitored by TLC). At thistime, the solvent was removed in vacuo and the residue was purifiedby flash column chromatography (the crude residue was dry loadedon silica gel, 1:20 to 1:1, EtOAc/PE) to provide the desired products 3and 4 (Scheme 2, Tables 2, 3).1-Phenylpyridin-2(1H)-one (3aa)19Yield: 0.054 g (63%); orange solid; mp 94-95 C.1H NMR (500 MHz, CDCl3): delta = 7.50-7.47 (m, 2 H), 7.43-7.36 (m, 4 H),7.34 (d, J = 8.5 Hz, 1 H), 6.66 (d, J = 10.5 Hz, 1 H), 6.25 (t, J = 7.0 Hz, 1 H).13C NMR (125 MHz, CDCl3): delta = 162.3, 140.9, 139.8, 137.9, 129.2,128.4, 126.4, 121.8, 105.8.

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 66171-50-4, Methyl 6-hydroxynicotinate.

Reference:
Article; Li, Xiao-Hua; Ye, Ai-Hui; Liang, Cui; Mo, Dong-Liang; Synthesis; vol. 50; 8; (2018); p. 1699 – 1710;,
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.55758-02-6, name is 3-Bromopicolinonitrile, molecular formula is C6H3BrN2, molecular weight is 183.01, as common compound, the synthetic route is as follows.Computed Properties of C6H3BrN2

EXAMPLE 178 COMPOUND 178:N1[3-(3.4-Dihydro-2H-guinolin-1-yl)-pyridin-2-ylmethyl]-N1-(3,5-dimethyl-pyridin-2-ylmethyl)-butane-1,4-diamine (HCl salt) A 250 mL round bottom flask was fitted with a magnetic stirrer and a reflux condenser (with a septum and N2 inlet on top). Cs2CO3 (13.04 g, 40 mmol), 3-bromopyridine-2-carbonitrile (2.66g, 20 mmol), toluene (100 mL), 1,2,3,4-tetrahydroquinoline (2.76 mL, 22 mmol), and 4,5-bis-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene (174 mg, 1.5% mol) were added in sequence. The mixture was degassed at room temperature by bubbling N2 through the suspension with stirring for 5 minutes. Pd2(dba)3 (90 mg, 0.5% mol) was added and the mixture was degassed again for 1 h at room temperature. The mixture was heated to 120 C. (bath) and refluxed under N2 in the dark. After two days, the mixture was cooled to room temperature. Another batch of 1,2,3,4-tetrahydroquinoline (2 mL), and Pd2(dba)3 (90 mg) were added. The system was degassed again for 1 h, and the heating was resumed. After another two days, the reaction mixture was cooled to room temperature and was concentrated by rotary evaporation under high vacuum. The residue was absorbed onto silica gel (50 mL) and loaded to a dry-packed silica gel column (200 mL silica). The column was eluted with 20% AcOEt/hexanes to afford a mixture of product and 3-bromo-2-cyanopyridine. The mixture was recrystallized from hexanes-AcOEt to give the product, 3-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-carbonitrile, as yellow crystals, 2.90 g (61.4%). 1H NMR (CDCl3) delta 2.06 (tt, 2H, J=5.7, 6.6 Hz), 2.91 (t, 2H, J=6.6 Hz), 3.76 (t, 2H, J=5.7 Hz), 6.56 (d, 1H, J=8.1 Hz), 6.85 (dd, 1H, J=0.9, 7.5 Hz), 6.98 (br, t, 1H, J=7.5 Hz), 7.10 (br, d, 1H, J=7.5 Hz), 7.42 (dd, 1H, J=4.5, 8.4 Hz), 7.72 (dd, 1H, J=1.2, 8.4 Hz), 8.42 (dd, 1H, J=1.5, 4.5 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55758-02-6, 3-Bromopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bridger, Gary; McEachern, Ernest J.; Skerlj, Renato; Schols, Dominique; US2004/209921; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 717843-48-6, name is 3-Bromo-6-methylpicolinonitrile. A new synthetic method of this compound is introduced below., Formula: C7H5BrN2

Under vacuum,Crystal water with a mass ratio of 40:60:8 g (36.1 mmol) of zinc chloride is heated to melt and remove water.Under nitrogen protection, 75 ml of 1,2-dichloroethane was added in sequence.Compound 3 is 3-bromo-6-methyl-2-cyanopyridine 5.5g(27.9mmol),13 g (77 mmol) of monomethyl malonate potassium salt and 1.8 ml (11.0 mmol) of diisopropylethylamine were stirred and refluxed for 16 hours.After the system was cooled to room temperature, 20 ml of 6N hydrochloric acid was added.Returning again for 1 hour, separating the organic phase,The aqueous phase was extracted 3 times with dichloromethane.The organic phases were combined and dried over anhydrous magnesium sulfate.Remove organic solvent, purify,The compound 4 is obtained as methyl 3-(3-bromo-6-methylpyridine)-3-carbonylpropanoate, the yield is 82%, 6.6 g;

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, 717843-48-6, 3-Bromo-6-methylpicolinonitrile.

Reference:
Patent; Chinese Academy Of Sciences Xinjiang Physics And Chemistry Technology Institute; A Jiaikebaier·aisa; A Budula·yusupu; Huang Guozheng; Zhao Jiangyu; (20 pag.)CN108164461; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 133427-07-3 ,Some common heterocyclic compound, 133427-07-3, molecular formula is C9H8N2O2, 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.

[0310] Lithium hydroxide solution (2.5 mL, 1M in water) was added to a solution of the ester from preparation 8 (400 mg, 2.27 mmol) in methanol (5 mL) and the solution stirred at room temperature for 90 minutes. The solution was concentrated in vacuo to remove the methanol, the aqueous solution acidified using 2M hydrochloric acid, and the mixture concentrated in vacuo to give the title compound as a yellow solid. [0311] 1HNMR (DMSO-D6, 400 MHz): 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) [0312] MS TSP+ m/z 163 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,133427-07-3, its application will become more common.

Reference:
Patent; Pfizer Inc; US2005/20626; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1052271-60-9, 8-Bromoimidazo[1,5-a]pyridine, 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, 1052271-60-9, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5BrN2

To a suspension of 8-bromoimidazo[1,5-a]pyridine [1,5-a]pyridine (290 mg, 1.5 mmol), N-(4-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)-2-(trifluoromethyl)benzamide (500 mg, 1.2 mmol), potassium carbonate (170 mg, 1.2 mmol) in DMF/Water (9: 1) palladium catalyst (5 mol%) was added. The reaction mixture was heated at about 11 0C for about 60 min. The reaction was diluted with ethyl acetate, filtered through celite, washed with water, brine and concentrated. The residue was was purified by prep HPLC using Gilson reverse phase eluting with ACN and water with 0.1% TFA using Luna column to get the N-(4-tluorophenyl)-5-(imidazo[1,5-a]pyridin-8-yl)-2(trifluoromethyl)benzamide ( 490 mg, 66% yield). 400.1 (M+ 1 ). 1H NMR ( 400 MHz, DMSO-d6) 8 10.74 (s, 1H), 9.08 (s, 1H), 8.54 (d, J = 7.0 Hz, 1H), 8.127.99 (m, 3H), 7.95 (s, 1H), 7.76- 7.68 (m, 2H), 7.27 {d, J = 6.8 Hz, 1H), 7.21 {t, J = 8.9 Hz, 2H), 7.04 (t, J = 7.0 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1052271-60-9, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BARTLETT, Mark, J.; CORKEY, Britton, Kenneth; COSMAN, Jennifer, Leigh; ELBEL, Kristyna, M.; ELZEIN, Eifatih; KALLA, Rao, V.; KOLTUN, Dmitry; LI, Xiaofen; PARKHILL, Eric, Q.; PERRY, Thao; (306 pag.)WO2019/40102; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6332-56-5, 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. 6332-56-5, name is 3-Nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

2-Hydroxy-3-nitro-pyridine (75 g, 0.535 mole) and 1400 ML of anhydrous tetrahydrofuran were stirred at 0 C. using a mechanical stirrer.. lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 683.5 ML) was slowly added over 30 minutes.. The deep brown reaction mixture was stirred for 30 additional minutes and then t-butyl bromoacetate (109.6 g, 0.561 mole) was slowly added over 30 minutes.. The reaction mixture was warmed to 25 C. overnight.. The organic solvents were removed under vacuum and the residue was dissolved in 2 liters of ethyl acetate and 500 ML of water.. The organic phase was dried with magnesium sulfate, filtered and evaporated under vacuum.. The residue was chromatographed on silica gel using a methylene chloride:ethanol gradient, 100:0 to 98:2, to yield 102.1 g (75 %) of the title compound as a yellow-orange solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6332-56-5, 3-Nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Corvas International, Inc.; US6342504; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem