Category: pyridine-derivatives

Electric Literature of 889676-37-3 ,Some common heterocyclic compound, 889676-37-3, molecular formula is C6H5BrN2O, 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.

Example 1-11: tert-Butyl 6-r5-carbamoylpyridin-2-ylV4-oxospirorchroman-2,4′-pirhoeridmel-r-carboxylatel’-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)spiro[chroman-2,4′-piperidm]-4-one (40.0 g, 90.0 mmol), 6-chloronicotinamide (17.0 g, 108 mmol), Pd(PPh3)4 (5.21 g, 4.51 mmol), and aqueous 2M Na2CO3 (100 ml) solution were suspended in dioxane (300 ml) and heated at 100C for 16 h. The reaction mixture was diluted with CEtaCI3 and H2O, the aqueous layer was extracted with CHCI3. The combined organic layer was washed with brine, dried over MgSCvj. and silicagel. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by crystallization (CHCI3 -EtOAc) to obtain the intended compound as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,889676-37-3, its application will become more common.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; JONA, Hideki; SHIBATA, Yoshihiro; YAMAKAWA, Takeru; WO2010/2010; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13362-78-2, 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 13362-78-2 as follows.

A mixture of ZnSO4* 7H2O (0.05mmol, 0.010g), H2L (0.025mmol ,0.006g), DPE (0.025mmol 0.005g), NaOH (0.025mmol,0.001g) and H2O (8mL) was sealed in a Teflon-lined autoclave and heated at 120 °C for 3 days,then followed by slow cooling to room temperature. The yield of the colorless block crystals is ca.68percent based on H2L. Elemental Anal. Found:C, 55.8;H,3.5;N,8.1percent. Calcd. for ZnC25H21N3O7: C,55.5;H,3.9;N,7.8percent. IR(cm1) (seeFig.S1): 3325(s),3061(m),1637(s),1568(s),1418(m),1387(s),1336(m),1281(m),1194(s),1148(w),1037(m),1017(m),964(m),842(s),769(m),671(m),549(s),462(m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-78-2, its application will become more common.

Reference:
Article; Yan, Xingxiu; Qiu, Xiandeng; Yan, Zhishuo; Li, Hongjiang; Gong, Yun; Lin, Jianhua; Journal of Solid State Chemistry; vol. 237; (2016); p. 313 – 322;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884494-49-9, 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.884494-49-9, name is 2-Chloro-5-fluoro-4-iodopyridine, molecular formula is C5H2ClFIN, molecular weight is 257.432, as common compound, the synthetic route is as follows.

A batch with 2-chloro-5-fluoro-4-iodopyridine [CAS-RN: 884494-49-9] (3000 mg; 11.65 mmol), (4- fluoro-3-methoxyphenyl)boronic acid [CAS-RN: 854778-31-7] (1981 mg; 11.65 mmol) and [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) [CAS-RN: 72287-26-4] (952 mg; 1.17 mmol) in 1 ,2-dimethoxyethane (30.0 mL) and 2 M aqueous solution of potassium carbonate (23 mL) was degassed using argon. The batch was stirred under an atmosphere of argon for 4 hours at 100 C. After cooling, the batch was diluted with ethyl acetate and THF and washed with a saturated aqueous solution of sodium chloride. The organic layer was filtered using a Whatman filter and concentrated. The residue was purified by column chromatography (hexane to hexane / ethyl acetate 50%) to give the title compound (2600 mg; 10.2 mmol). ‘H-NMR (400MHZ, DMSO-de): delta [ppm]= 3.92 (s, 3H), 7.28 (ddt, 1H), 7.39 (dd, 1H), 7.48 (dd, 1H), 7.86 (d, 1H), 8.55 (d, 1H).

Statistics shows that 884494-49-9 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-fluoro-4-iodopyridine.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; LUeCKING, Ulrich; HOG, Daniel; CHRIST, Clara; SACK, Ulrike; SIEGEL, Franziska; LIENAU, Philip; WERBECK, Nicolas; (195 pag.)WO2018/177899; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 70201-43-3 ,Some common heterocyclic compound, 70201-43-3, molecular formula is C6H4BrNO, 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.

General procedure: To a 50 mL round-bottomed flask charged with pentahydratedbismuth nitrate (0.032 g, 0.065 mmol) in ethanol(20 mL) were added thiobarbituric acid (0.144 g, 1.0 mmol) and aromatic aldehydes (1.0 mmol). The reaction mixturewas stirred for 10-20 min at 80 C, when thin layer chromatographyanalyzes revealed it was completed. Aftercompletion the precipitated product was separated by filtration,dried, and recrystallized from ethanol. Full physicaland spectroscopic data and yields for all compounds arepresented in the supporting information (SI).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70201-43-3, its application will become more common.

Reference:
Article; Shabeer, Muhammad; Barbosa, Luiz C. A.; Karak, Milandip; Coelho, Amanda C. S.; Takahashi, Jacqueline A.; Medicinal Chemistry Research; vol. 27; 4; (2018); p. 1043 – 1049;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10366-35-5, 2-Chloronicotinamide, 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: C6H5ClN2O, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5ClN2O

General procedure: To a solution of the corresponding amide (2 mmol) in THF (10 mL) was added chlorocarbonylsulfenyl chloride (350 muL, 4 mmol). The mixture was stirred at ambient temperature for 16 h. The solvent was removed in vacuo and the crude products were puried by silica-gel column chromatography using ethyl acetate/hexane as eluent solvent system.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10366-35-5, 2-Chloronicotinamide, and friends who are interested can also refer to it.

Reference:
Article; Yang, Jianzhong; Pi, Weiyi; Xiong, Li; Ang, Wei; Yang, Tao; He, Jun; Liu, Yuanyuan; Chang, Ying; Ye, Weiwei; Wang, Zhenling; Luo, Youfu; Wei, Yuquan; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1424 – 1427;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63897-12-1, 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. 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 3 3-Amino-2,4-bis(methylthio)-6-methylpyridine To a solution of 15.5 g (0.22 mol) sodium methanethiolate in 200 ml methanol was added slowly with stirring under nitrogen a solution of 20.8 g (0.1 mol) 3-nitro-2,4-dichloro-6-methylpyridine in 150 ml methanol. A precipitate formed and the mixture was stirred overnight at room temperature. The mixture was then filtered and the solid was washed first with methanol and then with water. 3-Nitro-2,4-bis(methylthio)-6-methylpyridine (18.9 g, 82% yield) was obtained as a yellow solid, mp 172-176C. 1 H NMR (CDCl3): delta2.45 (s, 3H); 2.51 (s, 3H); 2.55 (s, 3H); 6.77 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63897-12-1, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5596001; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80194-69-0, 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 80194-69-0, name is 5-(Trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (1S, 4S)-2-{(15)-1-[4-(allyloxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo-[2.2.1]heptane (7.3 g, 25.5 mmol), 5-(trifluoromethyl)pyridine-2-carboxylic acid (4.97 g, 26.0 mmol), BOP (16.9 g, 38.3 mmol) and NEt3 (8.89 mL, 63.8 mmol) in N,N-dimethylacetamide (50 mL) is heated at 40 C. under N2 overnight. The reaction mixture is cooled to room temperature, diluted with 1N NaOH (100 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, water and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue is purified by silica gel chromatography with EtOAc as the eluent to afford the title compound as a brown oil. 1HNMR (400 MHz, CDCl3) delta: 8.86 (s, 0.67H), 8.83 (s, 0.33H), 8.02-8.13 (m, 2H), 7.28 (m, 1H), 6.72 (m, 1H), 6.07 (m, 1H), 5.43 (m, 1H), 5.26 (m, 1H), 4.97 (s, 1H), 4.49-4.53 (m, 2H), 3.72-4.00 (m, 2H), 3.52 (m, 1H), 3.35 (m, 1H), 3.22 (m, 1H), 2.83 (d, 0.67H), 2.78 (d, 0.33H), 2.33 (s, 2H), 2.25 (s, 1H), 2.21 (s, 2H), 2.19 (s, 1H), 1.95 (m, 1H), 1.72 (m, 1H), 1.25-1.31 (m, 31). LC-MS m/z (M+H): 460.

According to the analysis of related databases, 80194-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hutchinson, Alan J.; Chenard, Bertrand L.; Li, Guiying; Ghosh, Manuka; Tarrant, James G.; Yoon, Taeyoung; Luke, George P.; Lee, Kyungae; O’Donnell, Mary-Margaret E.; Pringle, Wallace C.; Peterson, John M.; Hodgetts, Kevin J.; Steenstra, Cheryl K.; Doller, Dario; US2006/9456; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-10-3, 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. 63071-10-3, name is (4-Chloropyridin-2-yl)methanol, molecular formula is C6H6ClNO, 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 61 1-(4-(4-(2-(hydroxymethyl)pyridin-4-yl)benzyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide A microwave vial was charged with Intermediate III (60 mg, 0.144 mmol), (4-chloro-2-pyridinyl)methanol (24.77 mg, 0.173 mmol), K3PO4 (92 mg, 0.431 mmol), second generation Xphos Precatalyst (11.31 mg, 0.014 mmol), water (0.5 mL), THF (2 mL), and was evacuated and degassed with N2 for 5 min. The mixture was heated in the microwave at 100 C. for 2 hr, cooled to RT, and concentrated in vacuo. The resulting crude product was purified by FCC (gradient 2%-10% MeOH in DCM) then by preparative HPLC to afford 1-(4-(4-(2-(hydroxymethyl)pyridin-4-yl)benzyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide (2 mg, 3%): LCMS Rt=1.23 min (condition A), MS (M+1)=399.4. 1H NMR (400 MHz, Methanol-d4) delta 8.48 (dd, J=5.3, 0.8 Hz, 1H), 7.82 (dd, J=1.8, 0.9 Hz, 1H), 7.78-7.66 (m, 2H), 7.57 (dd, J=5.3, 1.9 Hz, 1H), 7.51-7.30 (m, 6H), 6.68 (d, J=0.9 Hz, 1H), 4.75 (s, 2H), 4.14 (s, 2H), 2.33 (d, J=0.7 Hz, 3H).

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 63071-10-3, (4-Chloropyridin-2-yl)methanol.

Reference:
Patent; NOVARTIS AG; DALES, Natalie; GORMISKY, Paul; KERRIGAN, John Ryan; SHU, Lei; (159 pag.)US2019/77773; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 10386-27-3, 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. 10386-27-3, name is 2-Bromoisonicotinonitrile, molecular formula is C6H3BrN2, 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.

StepD: (4S)-tert-Butyl 4-((l-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino) -2-oxoethyl){3- fluorophenyl)carbamoyl)-3-(4-cyanopyridin-2-yl)-2-oxoimidazolidine-l-carboxylate. To a 25 mL flask charged with 1,4-dioxane (4.5 mL) were added(4S)-tert-butyl4-((l-(2-chlorophenyI)- 2-(33-difluoro cyclo butylamino)-2-oxoethyl)(3-fiuoro -phenyl)carbamoyl)-2-oxoimidazolidine- 1- carboxylate (250 mg, 0.43 mmol), 2-bromoisonicotinonitrile (122 mg 0.65 mmol), CS2CO3 (281 mg, 0.862 mmol), Xant-Phos (25 mg 0.043 mmol) and Pd2(dba)3 (40 mg, 0.043 mmol). The mixture was degassed and refilled with nitrogen, and then heated to 100 °C for 3 hr. The resulting mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was purified by a standard method to give both epimers. The epimers were further separated by a standard method to give the desired product. ‘HNMR (400 MHz, CDC13): delta 8.58 (s, 1H), 8.48 (t, J= 5.9 Hz, 1H), 7.71 (d, J= 8.4 Hz, 1H),7.37 – 7.16 (m, 4H), 7.15 – 6.76 (m, 4H), 6.56 – 6.31 (m, 2H), 4.95 – 4.75 (m, 1H), 4.31 (s, 1H), 3.86 (dd,J= 10.8, 5.1 Hz, 1H), 3.66 (m, 1H), 2.99 (m, 2H),2.61 -2.27 (m, 2H), 1.56 (s,9H).MS : 683(M + 1)+.

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 10386-27-3, 2-Bromoisonicotinonitrile.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 791644-48-9 ,Some common heterocyclic compound, 791644-48-9, molecular formula is C6H2ClFN2, 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 solution of compound 4 (50 g, 321.7 mmol) in 1- butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol) , and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2x) and Et2<0 (2x) and dried in vacuo overnight to give compound 5 (44 g, 88%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): delta 5.53 (s, 2H); 7.94 (dd, IH); 8.35 (dd, IH); 12.02 (s, IH). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,791644-48-9, its application will become more common. Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem