Pyridine-derivatives

Electric Literature of 52605-96-6 , The common heterocyclic compound, 52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, 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.

V.16; 2-(3-methoxypropyl)pyridin-3-yl trifluoromethanesulfonate; Step 1: 3-methoxy-2-(3-methoxyprop-l-yn-l-yl)pyridine; To a solution of commercially available 2-chloro-3 ethoxy pyridine (1 eq.) in acetonitrile (1.9M) was added PdC12(CH3CN)2 (0.015 eq.), Cs2CO3 (2.4 eq.) and 2-(dicyclohexylphosphino)-2′-6′- 0 dimethoxy-l-l’-biphyl (S-PHOS; 0.044 eq.). The suspension was sonicated for 5min then 3- methoxyprop-1-yne (1.7 eq.) was added. The final mixture was stirred 12 h at 1000C, cooled down to room temperature, diluted with diethylether. The organic fraction was washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/ Acetone 5% afforded the desired compound.

The synthetic route of 52605-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/23964; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3430-21-5, 5-Bromo-3-methylpyridin-2-amine, 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, 3430-21-5, blongs to pyridine-derivatives compound. COA of Formula: C6H7BrN2

To a mixture of compound 4b1 (600 mg, 3.2 mmol) and concentrated H2SO4 (1.6 mL) and water (18.4 mL) is added drop wise a solution of NaNO2 (243.5 mg, 3.53 mmol) in water (1.6 mL) at 00C. After 30 min at room temperature the reaction is filtered and the resulting solid is washed with water and dried under high vacuum to give compound 4b2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-21-5, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2008/67644; (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. 113713-60-3, name is 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine

General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields).

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, 113713-60-3, 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine.

Reference:
Article; Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 26; 5; (2016); p. 1371 – 1375;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 28733-43-9, 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. 28733-43-9, name is 5-Bromonicotinamide, molecular formula is C6H5BrN2O, 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.

Bromine (18.76 g, 117.4 mmol) was added to a solution of sodium hydroxide (23.88 g, 597 mmol) in water (200 mL). To this solution was added 5-bromonicotinamide (20.00 g, 99.49 mmol). The reaction mixture was heated to 75 C. for 45 minutes. The reaction was cooled and acidified with concentrated hydrochloric acid. Some insoluble material was present. The insolubles were removed by filtration. The solution was washed with ethyl acetate (150 mL, 2 times). The aqueous solution was basified with sodium hydroxide solution (pH 10). The mixture was extracted into ethyl acetate (200 mL, 2 times). The ethyl acetate was dried and condensed to yield compound A (10.07 g, 58.5% yield).

According to the analysis of related databases, 28733-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2009/170886; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, 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, name: 2-Chloro-3-fluoro-5-nitropyridine, blongs to pyridine-derivatives compound. name: 2-Chloro-3-fluoro-5-nitropyridine

Step 2: To a stirred solution of 2-chloro-3-fluoro-5-nitropyridine (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) was added tributylvinyltin (3.42 g, 10.8 mmol) and Pd2(dba)3 (0.42 g, 0.45 mmol), trifuryl phosphene (0.2 g, 0.9 mmol) under nitrogen atmosphere. The reaction mixture was deoxygenated thoroughly and was heated to 60 C. for 6 h. The reaction mixture was diluted with water (20 mL) and was extracted with ethyl acetate (3*25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5% ethyl acetate in hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine. (1.5 g, 96%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/29961; (2013); 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. 1060805-95-9, name is 4-Chloro-6-methylnicotinic acid, the common compound, a new synthetic route is introduced below. Formula: C7H6ClNO2

To a solution of 4-chloro-6-methylnicotinic acid(0.1 g, 0.58 mmol) in ethanol (10.0 mL) was added SOCl2 (0.25 mL,3.49 mmol) at 0 C and the reaction mixture was stirred at 85 C for 12 h. Thereaction mixture was concentrated and the crude product was dissolved in EtOAc,washed with water, brine, dried over anhydrous Na2SO4,filtered and concentrated. The crude residue was purified by Combiflashpurifier with 5% MeOH in DCM to afford the title compound as off-white solid(0.1 g, 82 %). 1H NMR (DMSO-d6,400 MHz) delta 1.26 (t, J = 6.8 Hz, 3H), 1.32 (t, J = 7.2 Hz, 3H), 2.44 (s, 3H), 4.12-4.17(m, 2H), 4.20-4.26 (m, 2H), 7.03 (s, 1H), 8.56 (s, 1H); MS (ESI) m/z 210.1 (M+H)+.

The synthetic route of 1060805-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ruf, Sven; Hallur, Mahanandeesha Siddappa; Anchan, Nisha K.; Swamy, Indu N.; Murugesan, Karthikai Raj; Sarkar, Sayantani; Narasimhulu, Lokesh Kananti; Putta, V.P. Rama Kishore; Shaik, Shama; Chandrasekar, Devaraj Venkatapura; Mane, Vishal Subhash; Kadnur, Sanjay Venkatachalapathi; Suresh, Juluri; Bhamidipati, Ravi Kanth; Singh, Manvi; Burri, Raghunadha Reddy; Kristam, Rajendra; Schreuder, Herman; Czech, Joerg; Rudolph, Christine; Marker, Alexander; Langer, Thomas; Mullangi, Ramesh; Yura, Takeshi; Gosu, Ramachandraiah; Kannt, Aimo; Dhakshinamoorthy, Saravanakumar; Rajagopal, Sridharan; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 922 – 925;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6945-67-1, Adding some certain compound to certain chemical reactions, such as: 6945-67-1, name is 2-Bromo-4-nitropyridine,molecular formula is C5H3BrN2O2, 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 6945-67-1.

The crude title compound from Step A above was dissolved in a mixture of degassed 1,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 ,1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~115C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford a mixture of the title compound and byproducts (0.076 g).

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. 6945-67-1, 2-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; DARMENCY, Vincent; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; GABELLIERI, Emanuele; (93 pag.)WO2018/15549; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60781-83-1, 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. 60781-83-1, name is 4-Phenylpyridin-2-amine, molecular formula is C11H10N2, 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.

To a solution of (R)-4-BOC-2-morpholinecarboxylic acid (CAS Number 884512-77-0; 0.250 g, 1 .08 mmol) in DMF (15 ml) was added HATU (0.617g, 1 .62 mmol) at rt. The reaction mixture was stirred at rt for 30 min. 4-Phenylpyridin-2- ylamine (CAS Number 60781 -83-1 ; 0.184 g, 1 .08 mmol) and TEA (0.46 ml, 3.246 mmol) were added and the reaction mixture was stirred at rt for 72 h. The resulting reaction mixture was poured into water (25 ml) and extracted with EtOAc (3 x 25 ml). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (4% MeOH in DCM) yielding tert-butyl (R)-2-((4-phenylpyridin-2-yl)carbamoyl)morpholine- 4-carboxylate (0.1 15 g, 0.300 mmol). LCMS: Method C, 2.423, MS: ES+ 384.38; 1 H NMR (400 MHz, DMSO-d6) delta ppm: 9.86 (s, 1 H), 8.41 (d, J=5.2 Hz, 1 H), 8.36 (s, 1 H), 7.74 (d, J=6.8 Hz, 2 H), 7.48 – 7.57 (m, 4 H), 4.17 – 4.20 (m, 1 H), 4.01 – 4.03 (m, 2 H), 3.71 – 3.74 (m, 1 H), 3.53 – 3.58 (m, 1 H), 2.89 – 3.01 (m, 2 H), 1 .42 (s, 9 H).

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 60781-83-1, 4-Phenylpyridin-2-amine.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (167 pag.)WO2018/65768; (2018); 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. 28733-43-9, name is 5-Bromonicotinamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 28733-43-9

EXAMPLE P; 3-Bromo-5-fluoropyridine; Step 1; 3-Amino-5-bromopyridine; To a ice-cold solution of 31.8 g (0.79 mol) of Sodium hydroxide and 40.7 g (0.255 mol) of Bromine in 340 ml of water were added 42.0 g (0.209 mol) of commercially available 5-Bromonicotinamide. The mixture was allowed to warm up to room temperature and then heated for 1 h at 70 C. The resulting brown suspension was allowed to cool to room temperature. The aqueous phase was saturated with brine and extracted three times with a 1:1 mixture of THF and t-Butyl-methyl ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vaccuo. Concentration in vaccuo yielded 39.1 g of a dark brown residue which was purified by flash chromatography (heptane/ethyl acetate 1:1) to yield the title compound as a brown solid (total 70.2 g, 70%)

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, 28733-43-9, 5-Bromonicotinamide.

Reference:
Patent; Buettelmann, Bernd; Ceccarelli, Simona Maria; Jaeschke, Georg; Kolczewski, Sabine; Porter, Richard Hugh Philip; Vieira, Eric; US2006/160857; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1352625-30-9, 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. 1352625-30-9, name is 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, molecular formula is C7H4BrFN2, 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.

c) 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine A mixture of 3-bromo-6-fluoropyrazolo[1,5-a]pyridine (Preparation 103b, 0.300 g, 1.4 mmol), potassium acetate (0.492 g, 5.0 mmol) and bis(pinacolato)diboron (2.77 g, 10.9 mmol) in 1,4-dioxane (5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.380 g, 0.33 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was purified by reverse phase chromatography (C-18 silica from Waters, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (0.130 g, 36%) as a yellow solid. LRMS (m/z): 263 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm (two sets of peaks are seen in the NMR due to the presence of both the boronate and boronic acid): NMR of boronate: 1.21 (s, 12H), 7.56 (m, 1H), 8.02 (m, 1H), 8.36 (s, 1H), 9.16 (m, 1H).; PREPARATION 104 2-(6-Fluoropyrazolo[1,5-a]pyridin-3-yl)-9-(tetrahydro-2H-pyran-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purin-8(9H)-one A mixture of 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (Preparation 3, 0.150 g, 0.39 mmol), 6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (Preparation 103, 0.183 g, 0.70 mmol) and potassium acetate (0.134 g, 1.37 mmol) in 1,4-dioxane (5 mL) and water (1.5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.040 g, 0.03 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated under microwave irradiation (“Initiator sixty” from Biotage) at 120 C under an atmosphere of argon. After 40 minutes, further 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (0.060 g, 0.16 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) were added and heating was continued for 90 minutes. The reaction mixture was evaporated and then was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and concentrated. The residue was purified by flash chromatography (3:1 to 2:1 hexanes/ethyl acetate) to give the title compound (0.096 g, 50%) as pale yellow solid. LRMS (m/z): 485 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 0.06 (s, 9H), 1.00 (t, 2H), 1.80 (m, 2H), 2.91 (dq, 2H), 3.49 (s, 2H), 3.68 (m, 2H), 4.22 (m, 2H), 4.63 (m, 1H), 5.25 (s, 2H), 7.38 (t, 1H), 8.40 (s, 1H), 8.52 (m, 1H), 8.65 (dd, 1H), 8.78 (s, 1H).

According to the analysis of related databases, 1352625-30-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem