Category: pyridine-derivatives

Synthetic Route of 1152617-24-7 ,Some common heterocyclic compound, 1152617-24-7, molecular formula is C5H4ClIN2, 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 mixture of Z l7c (6.95 kg, assay 72%, 27.23 mol) in l,4-dioxane (72 L) was added Xantphos (233 g, 41 1 mmol, 0.015 eq), Pd2(dba)3 (186 g, 206 mmol,0.0075eq), Z l7b (7.13 kg, 28.02 mol) and DIPEA (7.02 kg, 54.46mol). The system was vacuated and purged with nitrogen gas three times. The mixture was stirred at 65 C for 16 h under N2. The mixture was cooled to rt and water (50 L) was added, filtered. The cake was washed with EA (25L). The filtrate was extracted with EA (4 x 20 L). The organic phase was concentrated in vacuum to offer the crude product which was combined with the cake. Then DCM (60 L) was added to the crude product and stirred at 25-30C for 18h and then filtered. The filter cake was slurried with CH2CI2 (30 L) for 4 hrs and filtered. The filter cake was slurred in CH2CI2 (30 L) for 16 hrs and filtered. Then the filter cake was dried in vacuum to give Z17a (9.1 kg, 84 %) as light yellow solid. NMR (400 MHz, DMSO-d6)5 = 7.89 (s, 1H), 7.7 (d, J = 7.6 Hz, 1H), 7.18 (bs, 2H), 6.40 (bs, 2H), 5.97 (d, J = 7.6 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,1152617-24-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 130658-65-0 ,Some common heterocyclic compound, 130658-65-0, molecular formula is C10H14N2O, 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.

The 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline used as a starting material was prepared as follows:- Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4 C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallized from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166 C. A 2.2M solution of hydrogen chloride in methanol (45 ml) was added over 15 minutes to a stirred solution in methanol (25 ml) of a portion (2.53 g) of the carbamate so obtained. The mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated and the residue was dissolved in water (50 ml). A 1M aqueous sodium hydroxide solution (25 ml) was added and the mixture was stirred for 1 hour. The precipitate was collected, washed with water and with diethyl ether and dried. There was thus obtained 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.71 g), m.p. 184-186 C.; NMR Spectrum 1.60 (m, 2H), 1.96 (m, 2H), 3.23 (m, 2H+H2O), 3.65 (m, 2H) 4.48 (m, 1H), 5.00 (s, 2H), 6.16 (m, 3H), 6.82 (d, 2H), 6.88 (t, 1H), 8.15 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130658-65-0, its application will become more common.

Reference:
Patent; ZENECA LIMITED; US2003/207882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17880-61-4, 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 17880-61-4, name is Methyl 5-ethynylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Sodium 5-[4′-(4′-aminophenyl)buta-1 ‘,3’-diyn-1 -yl]pyridine-2-carboxylate (144): Copper (II) acetate (1 .36 g, 7.46 mmol, 2.0 equiv) is added at room temperature under stream of argon to a stirred solution of 142 (0.60 g, 3.73 mmol) and 4- ethylnylbenzenamine (2.18 g 18.63 mmol, 5.0 equiv) dissolved in anhydrous pyridine (10 mL) and MeOH (10 mL). The reaction mixture is stirred at room temperature for 20 h. The resulting suspension is filtered, and the solid is washed with EtOAc (3^50 mL). The solid is dried under high vacuum for 12 h to afford as an orange powder, and then used for next step directly. 4N NaOH (10 mL) is added to a stirred solution of the crude methyl ester (600 mg) in MeOH (50 mL) at room temperature. Then reaction solution is heated to reflux for 40 min under argon. The reaction mixture turned clear. After all the starting material has been consumed monitored by TLC,the reaction mixture is cooled to room temperature, and the solvents are removed by evaporation under reduced pressure. The yellow solid is washed by water (3^50 mL), EtOAc (3×50 mL) to give a yellow solid (320 mg, 31 % yield, for two steps ), which is used for next step without future purification. 1 H NMR (300 MHz, CD3OD) 56.62 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 7.59 (d, J=9.0 Hz, 1 H), 8.27 (d, J=10.2 Hz, 1 H), 9.01 (s, 1 H); 13C NMR (75 MHz, CD3OD) 570.50, 75.996, 78.48, 85.59, 107.59, 1 14.17, 127.44, 133.09, 134.06, 137.62, 142.94, 150.69, 170.58; MS (ESI, positive): m/z 263 [M+H+].

According to the analysis of related databases, 17880-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUKE UNIVERSITY; ZHOU, Pei; TOONE, Eric, J.; WO2012/31298; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6000-50-6, 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 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-aminophenyl)-4-{1-[(4-methylphenyl)sulfonyl]-1H-indol-5-yl}pyridazin- 3(2H)-one (200 mg, 0.438 mmol) in dichloromethane (16.2 mL) and N,N-dimethylformamide (4.00 mL) was added pyridine (71.0 muL, 0.876 mmol) followed by portion wise addition of 4- nitrophenyl carbonochloridate (106 mg, 0.526 mmol) over 1 minute, and the reaction mixture stirred at r.t. for1 hour. To this reaction mixture was added N,N-diisopropylethylamine (381 muL, 2.19 mmol) followed by 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (169 mg, 0.876 mmol) under argon and the reaction mixture stirred at r.t. for 16 hours. The reaction mixture was combined with another batch (0.219 mmol), and concentrated to give a residue. The crude residue was triturated with water-ethanol and the resulting precipitate collected by filtration, washed with ethyl acetate, diethyl ether and dried to give 246 mg (90% purity,63% combined yield over two steps) of the desired product as pale yellow solid. (0981) LC-MS (Method 5): Rt = 0.85 min; MS (ESIpos): m/z = 603 [M+H]+ (0982) 1H-NMR (400 MHz, DMSO-D6) delta (ppm): 2.29 (s, 3H), 4.80 (d, 4H), 6.90 (s, 1H), 7.37 (d, 2H), 7.53-7.54 (m, 1H), 7.60-7.66 (m, 2H), 7.83-7.97 (m, 5H), 8.10 (s, 2H), 8.24 (s, 1H), 8.53- 8.55 (m, 1H), 8.63-8.65 (m, 2H).

According to the analysis of related databases, 6000-50-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, 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, HPLC of Formula: C9H9NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C9H9NO3

General procedure: A solution of the amidine 6 (1.1 equiv, 276 mg, 1.23 mmol) and the beta-ketoester 8a (1 equiv, 200 mg, 1.12 mmol) in nBuOH (3 mL) was stirred at 110 C for 18 h. During this time a solid precipitate formed. After cooling to room temperature, the solid was filtered off and air-dried to provide 9a (190 mg, 48%) as a pale yellow solid;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, and friends who are interested can also refer to it.

Reference:
Article; Large, Jonathan M.; Torr, Jane E.; Raynaud, Florence I.; Clarke, Paul A.; Hayes, Angela; Stefano, Francesca Di; Urban, Frederique; Shuttleworth, Stephen J.; Saghir, Nahid; Sheldrake, Peter; Workman, Paul; McDonald, Edward; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 836 – 851;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 865156-50-9, Adding some certain compound to certain chemical reactions, such as: 865156-50-9, name is (4-Bromopyridin-2-yl)methanamine,molecular formula is C6H7BrN2, 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 865156-50-9.

d) N-(4-Bromopyridin-2-ylmethyl) formamide; 20. 00 g of C-(4-bromopyridin-2-yl)methylamine are taken up in 60 ml of formic acid and the solution is heated to reflux over 3 hours. The reaction solution is cooled to room temperature and concentrated by evaporation, and the residue is taken up in saturated aqueous sodium hydrogencarbonate solution {300 mu) and the aqueous solution is extracted with dichloromethane (3×300 mi). The combined organic phases are washed with water (300 mi), dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F)

According to the analysis of related databases, 865156-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); 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.18364-47-1, name is N-Methylpyridin-3-amine, molecular formula is C6H8N2, molecular weight is 108.14, as common compound, the synthetic route is as follows.HPLC of Formula: C6H8N2

Stage 13-Bromo-4-methoxy-N-methyl-N-pyridin-3-ylbenzamide An amount of 5 g (22 mmol) of 3-bromo-4-methoxybenzoic acid was dissolved in 50 ml of dichloromethane with 8.3 g (65 mmol) of diisospropylethylamine, and the solution was admixed with 5.8 g (23 mmol) of BOP-Cl and then with 2.5 g (24 mmol) of methylpyridin-3-ylamine and stirred for 2 days. The mixture was concentrated, the residue was admixed with water and aqueous sodium chloride and extracted three times with ethyl acetate, and the combined organic phases were dried and concentrated by evaporation. The residue was purified by chromatography on silica gel (cyclohexane/acetone).Yield: 5.49 g (74% of theory), 1H-NMR (D6-DMSO) 3.35 (s, 3H), 3.8 (s, 3H), 6.95 (d, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.5 (m, 1H), 7.7 (m, 1H), 8.35 (m, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18364-47-1, N-Methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/305124; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84487-10-5, Adding some certain compound to certain chemical reactions, such as: 84487-10-5, name is 2-Amino-4-bromo-3-nitropyridine,molecular formula is C5H4BrN3O2, 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 84487-10-5.

Step 1 (0852) A solution of 4-bromo-3-nitropyridin-2-amine (LXVI) (5.00 g, 22.9 mmol, 1.00 eq), (2-fluorophenyl)boronic acid (LXVII) (3.82 g, 27.5 mmol, 1.20 eq), Pd(PPh3)4 (1.32 g, 1.14 mmol, 0.05 eq), and Na2CO3 (4.85 g, 45.8 mmol, 2 eq) in a mixture of toluene (25 mL), H2O (9 mL) and EtOH (6 mL) was stirred at 75 C. for 15 h under nitrogen atmosphere. The reaction mixture was the washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by chromatography on silica gel (PE:EtOAc=3:1) to give 4-(2-fluorophenyl)-3-nitropyridin-2-amine (LXVIII) (4.0 g, 17.15 mmol, 74.9%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta ppm 6.29 (brs, 2H), 6.68 (d, J=4.8 Hz, 1H), 7.14 (t, J=5.2 Hz, 1H), 7.23-7.50 (m, 3H), 8.32 (d, J=4.8 Hz, 1H); ESIMS found C11H8FN3O2 m/z 234.2 (M+H).

According to the analysis of related databases, 84487-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68551; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 874302-76-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 874302-76-8 as follows.

Weigh 61.2mg (0.06mmol) compound 39,64.3mg (0.18mmol) compound 37,9.8mg (0.08mmol) DMAP, was added to a 25ml eggplant-shaped flask, add 5ml DCM was dissolved under argon atmosphere, stirred at room temperature 48h, DCM was evaporated to dryness under reduced pressure and, add acetonitrile dissolved, purified by preparative liquid phase to give product 51.3mg

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874302-76-8, its application will become more common.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Liu Keliang; Feng Siliang; Chen Kuncheng; Guo Xiaopeng; Meng Qingbin; Zhou Ning; (23 pag.)CN104370862; (2019); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1001412-41-4, name is 5,7-Dichloro-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H4Cl2N2, 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. Safety of 5,7-Dichloro-1H-pyrrolo[2,3-c]pyridine

Step B: 5,7-dichloro-1 -methyl-pyrrolo[2,3-clpyridine: A solution of 5,7-dichloro-1 H-pyrrolo[2,3-c]pyridine (2 g, 10.693 mmol) in dry N,N- dimethylformamide (50 mL) was treated with sodium hydride (0.77 g, 16.04 mmol) at ambient temperature and reaction stirred for 15 min at this temperature. The reaction mixture was cooled to 0C and iodomethane (1 mL, 16.04 mmol) was added, and the mixture allowed to stir 18 hours at ambient temperature. The reaction mixture was then quenched with NH4CI saturated solution, extracted with ethyl acetate (three times), and the combined organic layer was dried over Na2S04, filtered and evaporated under vacuum. Purification by Combi flash chromatography with a column of 24g and a gradient cyclohexane:0-100% ethyl acetate to give the title compound as a yellow solid (1.8 g, 84%).

With the rapid development of chemical substances, we look forward to future research findings about 1001412-41-4.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; BIGOT, Aurelien; HALL, Roger Graham; JEANGUENAT, Andre; LUKSCH, Torsten; RENDLER, Sebastian; WO2013/156431; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem