Category: pyridine-derivatives

Application of 80194-68-9, 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, molecular formula is C7H3ClF3NO2, 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.

Production Example 17(1) A mixture of N2-methyl-5-pentafluoroethyl-pyridin-2 , 3- diamine (590 mg) , 3-chloro-5-trifluoromethyl-pyridin-2- carboxylic acid (560 mg) , WSC (520 mg) , HOBt (35 mg) , and pyridine (5 ml) was stirred at room temperature for 5 hours To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give intermediate compound (M20-17) .

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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; TANABE, Takamasa; ITO, Mai; NOKURA, Yoshihiko; IWATA, Atsushi; WO2013/18928; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 100366-75-4, 2-Iodo-5-trifluoromethylpyridine, 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, Recommanded Product: 2-Iodo-5-trifluoromethylpyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Iodo-5-trifluoromethylpyridine

General procedure: In a glove box, a flame-dried pressure Schlenk tube was charged with NaI(0.3 equiv). The Schlenk tube was taken out of the glove box and charged with amide 1 (1.5equiv), iodopyridine reagent (1 equiv), Ag2CO3 (1.5 equiv), (BnO)2PO2H (0.2 equiv) andPd(OAc)2 (0.1 equiv). DMA and Toluene (1:20 in v/v ratio, 0.1 M) were added. The tube wastightly closed and flushed with argon by three freeze-pump-thaw cycles. The mixture was stirredat 130 C for 24 h. Subsequently, it was diluted with EtOAc (40 mL) and washed with brine (2 ×20 mL) and water (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated invacuo. The crude product was purified by flash chromatography (hexane/ EtOAc in 85/15 to 50/50v/v ratio). Unless otherwise noted, the reactions were run on 0.1 mmol scale.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100366-75-4, 2-Iodo-5-trifluoromethylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Hu, Peng; Bach, Thorsten; Synlett; vol. 26; 20; (2015); p. 2853 – 2857;,
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.174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, molecular weight is 113.09, as common compound, the synthetic route is as follows.Quality Control of 2-Fluoropyridin-3-ol

A solution comprising 2,3,4,6-Tetra-O- acetyl-a-D-galactopyranosyl bromide 3 (1 .0 g, 2.4 mmol), Ag2C03 (0.74 g, 2.7 mmol), MS- 4A (5 g) and 2-fluoro-pyridin-3-ol 5 (0.33 g, 2.9 mmol) in anhydrous DCM (15 mL ) is stirred overnight, in the dark, at room temperature, under an argon atmosphere. TLC analysis indicated the complete consumption of the starting bromide and the formation of a new nonpolar product. The solution is filtered through a celite, which was rinsed with DCM (3 x 10 mL ). After removing the solvent under reduced pressure, the crude residue is purified directly using silica gel column chromatography, using an increasing gradient of EtOAc in PE. The product afforded is a colorless solid (0.51 g, 51 %). (0101) [0074] TLC: Rf = 0.5 (EtOAc: PE = 1 : 1 ); 1H NMR (600 MHz, Chloroform-d) delta 7.94 (d, J= 4.6 Hz, 1 H, ArH), 7.58 (t, J= 7.8 Hz, 1 H, ArH), 7.13 (dd, J= 7.8, 4.8 Hz, 1 H, ArH), 5.50 (dd, J= 10.5, 7.9 Hz, 1 H), 5.45 (d, J= 3.4 Hz, 1 H), 5.10 (dd, J= 10.5, 3.4 Hz, 1 H), 4.96 (d, J= 7.9 Hz, 1 H), 4.22 (dd, J= 1 1.4, 6.8 Hz, 1 H), 4.15 (dd, J= 1 1 .4, 6.3 Hz, 1 H), 4.01 (td, J = 6.8, 1 .1 Hz, 1 H), 2.19 (s, 3H, OAc), 2.1 1 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.02 (s, 3H, OAc); 13C NMR (151 MHz, CDCI3) delta 170.26 (COquart), 170.13 (COquart), 170.04 (COquart), 169.44 (COquart), 154.75 (d, J= 239.9 Hz), 141 .59 (d, J= 13.4 Hz, ArC), 139.49 (d, J= 25.5 Hz, ArC), 130.22 (d, J = 3.5 Hz, ArC), 121.85 (d, J = 4.3 Hz, ArC), 121.23 (CH), 101.12 (CH), 71.38 (CH), 70.5 (CH), 68.29 (CH), 66.70 (CH), 61.17 (CH2), 21.03 (OAc), 20.63 (OAc), 20.61 (OAc), 20.55 (OAc).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,174669-74-0, 2-Fluoropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; EBERHARD KARLS UNIVERSITAET TUEBINGEN MEDIZINISCHE FAKULTAET; COTTON, Jonathan; KUEHN, Anna; MAURER, Andreas; PICHLER, Bernd; SCHULZE-OSTHOFF, Klaus; FUCHS, Kerstin; KRUEGER, Marcel Andre; ZENDER, Lars; (42 pag.)WO2018/153966; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7295-76-3, 3-Methoxypyridine, 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, 7295-76-3, blongs to pyridine-derivatives compound. COA of Formula: C6H7NO

General procedure: [Li(TMP)Zn(tBu)2] 1 was made according to the literature procedure2 on a 0.4 mmol scale in THF solution. To this solution 3-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. This solution was then transferred to a THF (1 mL) solution of PdCl2(dppf) (29.3 mg, 10 mol %) and 1-bromo-4-chlorobenzene (76.6 mg, 0.4 mmol) to give a heterogeneous red solution. The reaction mixture was then reacted in the microwave at 100C for 10 minutes. The reaction was then quenched with saturated NH4Cl solution (2 mL) and extracted with DCM (3 x 1 mL). The organic fractions were combined and dried by passing through a phase separator cartridge with a hydrophobic frit and the solvent removed under reduced pressure. The residue was purified by column chromatography using a 4 g C18 silica cartridge and eluent Acetonitrile + 0.1 % formic acid:H2O + 0.1 % formic acid (5:95 to 95:5) to give compound 3b as an off white solid 26.5 mg (30% yield) 1H NMR (400 MHz, CDCl3) delta ppm 3.93 (s, 3H) 7.24 (d, J=4.69 Hz, 1 H) 7.39 – 7.46 (m, 2 H) 7.48 – 7.56 (m, 2 H) 8.33 (d, J=4.49 Hz, 1 H) 8.39 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7295-76-3, its application will become more common.

Reference:
Article; Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C.; Tetrahedron Letters; vol. 52; 36; (2011); p. 4590 – 4594;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58483-95-7 , The common heterocyclic compound, 58483-95-7, name is 5-Amino-2-chloropyridine-4-carboxylic acid, molecular formula is C6H5ClN2O2, 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.

6-Chloro-3H-pyrido[3,4-d]pyrimidin-4-one. A solution of 5-amino-2-chloropyridine-4-carboxylic acid (8.1 g, 4.7 mmol) in formamide (100 mL) is stirred at 140° C. for 12 h. Dilution of the cooled mixture with water gives a precipitate of 6-chloro-3H-pyrido[3,4-d]pyrimidin-4-one (7.3 g, 86percent yield). 1 H NMR (DMSO) delta 12.73 (1H, m), 8.90 (1H, d, J=0.7 Hz), 8.23 (1H, s), 7.97 (1H, d, J=0.7 Hz).

The synthetic route of 58483-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US5654307; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13143-47-0, 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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 1-(4-aminophenyl)pyridin-2(1H)-one (3a) (0.90 g, 4.8 mmol), K2CO3 (0.80 g, 5.8 mmol) and DMAP (0.05 g, 0.4 mmol) inTHF (20 mL), solution of 2-nitrobenzoyl chloride (2a) (1.15 g, 6.24 mmol) in THF (5 mL) was addedat room temperature and the mixture was refluxed for 2 h. The reaction mixture was cooled downto room temperature and concentrated under reduced pressure. Then water (100 mL) was addedto the mixture and stirred for 10 min at room temperature. The resulting precipitate was collectedby filtration. The reaction was monitored by TLC with EA.

The chemical industry reduces the impact on the environment during synthesis 13143-47-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Wenzhi; Yuan, Jing; Fu, Xiaoli; Meng, Fancui; Zhang, Shijun; Xu, Weiren; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 21; 4; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-84-1, 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. 128071-84-1, name is 4-Bromo-2-chloropyridine-3-carboxaldehyde. A new synthetic method of this compound is introduced below.

Example 104b 2-Chloro-4-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 104b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 104a (1.1 g, 5.0 mmol), 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101e (477 mg, 2.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (230 mg, 0.25 mmol), XantPhos (430 mg, 0.75 mmol), Cs2CO3 (1.6 g, 5.0 mmol), and 1,4-dioxane (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65C for 2 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (40:1) to afford 104b as a yellow solid (1.1 g, 80%). MS: [M+H]+ 330.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-84-1, its application will become more common.

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

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. 7584-05-6, name is 3-Methylisonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6N2

Preparation of (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile; [00150] To a solution of 3-methylisonicotinonitrile (10 g, 85 mmol) in DMF (100 mL) was added l,l-dimethoxy-N,N-dimethylmethanamine (18.05 mL, 135 mmol). The mixture was heated to reflux overnight. The mixture was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture, and it was again heated to reflux. After heating the mixture overnight, it was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture. The mixture was heated overnight at reflux. The mixture was cooled to rt and an additional 3.0 mL of 1 , 1 -dimethoxy-N,N- dimethylmethanamine were added. The mixture was again heated to reflux. After heating the mixture overnight, it was cooled to rt. To the mixture was added 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine. The mixture was heated to reflux overnight. The mixture was cooled to rt and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and was loaded onto a BIOTAGE 65 + M cartridge and was purified using a 10-70% EtOAc in hexanes gradient. The expected product, (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile (7.97 g, 46.0 mmol, 54.4 % yield), was isolated as a bright-yellow solid. LC/MS: m/z 174.11 (M+H)+ , 1.690 min (method 1). 1H NMR (500 MHz, chloroform-^) I ppm 1H NMR (500 MHz, chloroform-^ I ppm 8.69 (s, 1 H) 8.14 (d, J= 5.19 Hz, 1 H) 7.23 (d, J= 4.88 Hz, 1 H) 7.15 (d, J= 13.43 Hz, 1 H) 5.21 (d, J= 13.73 Hz, 1 H) 2.95 (s, 6 H)

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, 7584-05-6, 3-Methylisonicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158396; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5 , The common heterocyclic compound, 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, 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.

[0202] A solution of methyl 6~chloro-5-nitronicotinate (5 g, 23.09 mmol), 4~(2,,4~ difluorophenoxy)piperidine hydrochloride (6.92 g, 27.7 mmol) and K2CO3 (9.57 g, 69.3 mmol) in ACN (57.7 mL) was stirred at 80°C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 250 mL). The organic layers were combined, dried over NazSC and filtered. The filtrate was concentrated in vacuo and purified by column chromatography (ISCO column) elutmg with a gradient of 0-100percent EtOAc in heptane, to give the title compound as a yellow solid (6.04 g, 66.5percent). lR NMR (500 MHz, DMSO-afe) delta ppm 1.74 (dq,./ 12. KK. 4.17 Hz, 2 I .}. 2.04 (ddd, J=9.76, 6.83, 3,42 Hz, 2 H), 3.45 (td, 7=8.91, 4.15 Hz, 2 H), 3.71 – 3.76 (m, 2 H), 3.85 (s, 3 H), 4,66 (tt, J=7.51, 3,72 Hz, 1H), 7.00 – 7,06 (m, 1H), 7.27 – 7.36 (m, 2 H), 8.56 (d,/ 1.46 Hz, 1H), 8.82 (d,,/ 1.46 Hz, 1H); ESI-MS m/z | M I I . 394.2.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 186593-42-0, 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. 186593-42-0, name is 3-Bromo-2-methyl-5-nitropyridine. A new synthetic method of this compound is introduced below.

4-(2-Methyl-5-nitropyridin-3-yl)-N-neopentyIbenzenesulfonamide. The compound obtained above (30 mg, 0.085 mmol), 3-bromo-5-nitro-2-methylpyridine (1.0 eq., 18 mg), K2CO3 (3 eq., 35 mg) and Pd(PPh3)4 (10 mol %, 10 mg) were dissolved in 3 ml DMErEtOH (9: 1). The solution was stirred at 800C for 24 hr under nitrogen. The mixture was concentrated in vacuo. Column chromatography (SiOa; 3:1 Hex: EtOAc) yielded 20 mg of the target compound. (CaIc. mass: 364, obs. mass 364).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186593-42-0, 3-Bromo-2-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2008/21388; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem