Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 942947-94-6, 5-Bromo-4-chloropyridin-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, 942947-94-6, blongs to pyridine-derivatives compound. Computed Properties of C5H4BrClN2

Synthesis of 4-chloro-5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-2- pyridylamine[00100] To a dry 500-mL flask was added 5-bromo-4-chloro 2-pyridylamine (7.3 g, 35.8 mmol), potassium acetate (10.3 g, 105 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (10.1 g, 39.8 mmol) and dioxane (150 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (0.85 g, 1.04 mmol) was added. The reaction was refluxed in a 1 15 C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was then added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by Si02 chromatography (EtOAc as eluent). Upon removal of solvent, 3: 1 hexanes/CH2Cl2 was added (100 mL). After soni cation, the resulting solid was filtered and concentrated in vacuo yielding 2.8 g of a white solid. By ¾ NMR the material was a 10: 1 mixture of boronate ester and 2-amino-4-chloropyridine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z):173 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). ¾ NMR (CDCI3): delta 8.36 (s, 1H), 6.46 (s, 1H), 4.70 (bs, 2H), 1.38 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942947-94-6, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131803-48-0, Adding some certain compound to certain chemical reactions, such as: 131803-48-0, name is Methyl 6-(bromomethyl)nicotinate,molecular formula is C8H8BrNO2, 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 131803-48-0.

NaH (60%, 41.5mg, 1 .O4mmol) was added to a solution of (3) (200mg, 0.99mmol) in DMF (lOmL) at 5C under N2(g). The reaction mixture was stirred for 20 mm then methyl 4-(bromomethyl)benzoate (294mg, 1 .29mmol) was added. The stirring was continued at 70C under N2(g) for lh. The reaction was cooled to rt and poured onto water (l5OmL) and brine (5OmL), the aqueous was extracted with EtOAc (3 xlOOmL). Combined organics were dried over Na2504, filtered and concentrated invacuo. The residue was purified by flash column chromatography withCH2CI2/EtOAc (1:0-0:1) then EtOAc/MeOH (1:0-4:1) to yield (4) (251mg, 73%).1H NMR (500 MHz, Chloroform-d), OH ppm: 8.06-8.10 (m, 2H), 7.87-7.92 (m, 3H),7.78 (d, J=1.5 Hz, 1H), 7.44 (d, J=8.4 Hz, 2H), 7.23 (dd, J=8.2, 1.4 Hz, 1H), 7.15(dd, J=8.1, 4.7 Hz, 1H), 5.42 (5, 2H), 3.85 (5, 3H), 3.73 (5, 3H). LCMS (ES): Found 350.9 [M+H].

According to the analysis of related databases, 131803-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
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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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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-Bromo-1H-pyrrolo[2,3-b]pyridine

General procedure: To a solution of appropriate pyrrolo-pyridines 8a-f (2.5 mmol) in 10 mL of anhydrous DCM, anhydrous AlCl3 (1.2 g, 8.8 mmol) was slowly added. The reaction mixture was heated under reflux and BrCOCH2Br (2.5 mmol, 0.2 mL) in 2 mL of anhydrous DCM was added dropwise. The resulting solution was allowed to stir under reflux for 40 min. After cooling, water and ice were slowly added and the obtained precipitate (for derivative 9a) was filtered off or the oil residue (for derivatives 9b-f) was extracted with DCM (3 × 20 mL) and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent [42].

With the rapid development of chemical substances, we look forward to future research findings about 183208-35-7.

Reference:
Article; Carbone, Anna; Parrino, Barbara; Vita, Gloria Di; Attanzio, Alessandro; Span, Virginia; Montalbano, Alessandra; Barraja, Paola; Tesoriere, Luisa; Livrea, Maria Antonia; Diana, Patrizia; Cirrincione, Girolamo; Marine Drugs; vol. 13; 1; (2015); p. 460 – 492;,
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Reference of 878207-92-2, 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.878207-92-2, name is Methyl 6-chloro-3-methylpicolinate, molecular formula is C8H8ClNO2, molecular weight is 185.61, as common compound, the synthetic route is as follows.

To a stirred solution of methyl 6-chloro-3-methylpicolinate (1.0 g, 5.4 mmol) in 1,4-Dioxane (20 mL) were added, 2-(3-((4-Methoxybenzyl)oxy)-5-(trifluoromethyl)phenyl)-4,4,5,5-tetra methyl- 1, 3, 2-dioxaborolane (3.5 g, 8.6 mmol), Na2C03 (1.7 g, 16.2 mmol) in H20 (2 mL) and the mixture was degassed for 10 mins. To this, PdCl2(dppf) (0.16 g, 0.22 mmol) was added and the reaction mixture was heated to 100 C overnight. After completion (TLC), it was diluted with Ethyl acetate (50 mL) and filtered through a pad of celite. The filtrate was collected, concentrated and purified by flash chromatography using Ethyl acetate: Hexanes to afford the titled compound (1.2 g, 51%) as white solid.

The chemical industry reduces the impact on the environment during synthesis 878207-92-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUPIN LIMITED; MADAN, Sachin; TALE, Prashant, Vitthalrao; ZADE, Seema, Prabhakar; PATIL, Amolsing, Dattu; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2015/162538; (2015); A1;,
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Pyridine | C5H5N – PubChem

Application of 10128-91-3, Adding some certain compound to certain chemical reactions, such as: 10128-91-3, name is Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate,molecular formula is C7H7NO3, 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 10128-91-3.

Methyl 2-hydroxynicotinate (500 mg, 3.27 mmol) and N-bromosuccinimide (756 mg, 4.25 mmol) were dissolved in dichloromethane and the mixture was stirred at 50 C for 48 hours. The mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was filtered with a small amount of dichloromethane to obtain the title compound (0.3 g, yield: 40%, yellow solid). *H NMR (500MHz, DMSO-d6) d 8.07 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 3.75 (s, 3H)

According to the analysis of related databases, 10128-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WELLMARKER BIO CO., LTD.; LEE, Hyunho; PARK, Chun-Ho; HUR, Sun Chul; MOON, Jai-Hee; SHIN, Jae-Sik; HONG, Seung-Woo; PARK, Yoon-Sun; KIM, Joseph; LEE, Sohee; KIM, Hyojin; PARK, Hyebin; (83 pag.)WO2019/182274; (2019); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 6635-90-1, 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. 6635-90-1, name is 2-Methoxy-4-methyl-5-nitropyridine, molecular formula is C7H8N2O3, 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.

b 5-Amino-2-methoxy-4-methylpyridine A mixture of stannous chloride dihydrate (41 g) and concentrated hydrochloric acid (40 ml) was added slowly to a solution of 2-methoxy-4-methyl-5-nitropyridine (5.1 g) in acetic acid (40 ml), maintaining the temperature below 35 C. The resulting mixture was stirred at room temperature for 2 hours, and then allowed to stand overnight in the refrigerator. The solid was collected and both solid and supernatant were separately basified with a 20% sodium hydroxide solution. The product was extracted with chloroform, combined, dried (anhydrous magnesium sulfate) and concentrated to give 3.9 g of the title compound as a solid, suitable for use in the next reaction.

According to the analysis of related databases, 6635-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5366972; (1994); A;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 55304-75-1, Adding some certain compound to certain chemical reactions, such as: 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine,molecular formula is C6H2Cl2F3N, 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 55304-75-1.

Nine separate sealed tubes, each containing a mixture of 2,6-dichloro-3-(trifluoromethyl)pyridine (10.0g, 46.3 mmol) and ammonium hydroxide (91 g, 100 mL, 2600 mmol) were stirred at 100 C. for 12 h. After cooling to rt, the contents of all of the sealed tubes were combined and the solvents were concentrated in vacuo. Purification of the (FCC, SiO2; 5-20% EtOAc/petroleum ether) afforded the title compound as a colorless oil (57 g, 66%), which solidified upon standing. MS (ESI): mass calcd. for C6H4ClF3N2, 196.0; m/z found, 196.8 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.69 (d, J=8.0 Hz, 1H), 6.42 (d, J=8.4 Hz, 1H), 5.01 (br s, 2H).

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. 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
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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. 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C8H7N3

solid I (2.61 g, 18.0 mmol) was added to a solution of KOH in H2O (50%, 10 ml). 2-Chloromethyl ethyl ether (1.46 g, 15.4 mmol) was added dropwise and the reaction mixture was refluxed for 3.5 h. Water (10 ml) was added to the reaction mixture and the organic phase was separated. The aqueous layer was further extracted several times with DCM and the combined organic layer was washed with water and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (DCM:MeOH = 9:1). L2 was obtained as a slightly yellow liquid. Yield: 34%. 1H NMR (200.13 MHz, DMSO-d6): delta = 8.58 (ddd, 1 H, 6-pyH), 8.09 (ddd, 1 H, 3-pyH), 7.87 (ddd, 1 H, 4-pyH), 7.32 (d, 1 H, 5-imH), 7.34 (ddd, 1 H, 5-pyH), 7.03 (d, 1 H, 4-imH), 4.75 (t, 2 H, NCH2CH2OCH3), 3.65 (t, 2 H, NCH2CH2OCH3), 3.19 (s,3 H, CH3) ppm. 13C NMR (50.33 MHz, DMSO-d6): delta = 151.0 (2-pyC), 149.3 (6-pyC), 143.9 (2-imC), 137.8 (4-pyC), 128.5 (4-imC),125.5 (5-imC), 123.3 (5-pyC), 122.9 (3-pyC), 72.1 (NCH2CH2OCH3),58.6 (CH3), 47.6 (NCH2CH2OCH3) ppm (Fig. S35, Supporting information). IR (diamond, ATR): ~v = 2892, 1588 (s), 1566, 1486 (s),1459 (vs), 1407, 1298, 1277, 1211, 1117 (vs), 1038, 1012, 992, 969, 917, 833, 791 (vs), 743 (vs), 708 (vs), 667, 624, 404 cm-1 (Fig. S22, Supporting information). APCI-MS (MeOH) m/z (rel. abundance,fragment) = 204.1132 (100%, [HL2]+) (Fig. S8, Supporting information). Elemental analysis (%)Anal. Calc. for C11H13N3O(203.24 g mol1): C, 65.01; H, 6.45; N, 20.67. Found: C, 64.69; H,6.46; N, 20.79%. UV-Vis (MeCN): lambdamax(epsilon) = 294 (15,850), 266(12,180) nm (M-1 cm-1) (Fig. S37, Supporting information).

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, 18653-75-3, 2-(1H-Imidazol-2-yl)pyridine.

Reference:
Article; Huxel, Timo; Skaisgirski, Michael; Klingele, Julia; Polyhedron; vol. 93; (2015); p. 28 – 36;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 677728-92-6, 2-Fluoropyridine-5-carbaldehyde, 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, 677728-92-6, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Fluoropyridine-5-carbaldehyde

EXAMPLE 234. 5-(l,3-DIOXOLAN-2-YL)-2-FLUORO-3-(4,4,5,5-TETRAMETHYL-l,3,2- DIOXABOROLAN-2-YL)PYRIDINESTEP 1: 5-(l,3-DIOXOLAN-2-YL)-2-FLUOROPYRIDINE[00611 ] 6-Fluoronicotinaldehyde (21.96 g, 176 mmol) was suspended in toluene (340 mL) and ethylene glycol (10.4 mL, 186 mmol) and p-toluenesulfonic acid (Acros, 15% in acetic acid, 1.10 mL) were added. The flask was fitted with a Dean-Stark head and a reflux condenser, and placed in a preheated oil bath (120 0C) and the reaction was stirred. After 45 minutes, the reaction was cooled to room temperature. The reaction was diluted with saturated sodium bicarbonate (50 mL), water (150 mL) and EtOAc (150 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (600 mL fritted filter with about 3 inches of silica gel; DCM to 100: 1 to 50: 1 DCM / MeOH to 40: 1 DCM / MeOH) to give 19.055 g of 5-(l,3-dioxolan-2-yl)-2-fluoropyridine. m/z (ESI, +ve ion) 170 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1111637-68-3, 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 1111637-68-3 as follows.

To a solution of 5-bromo-3-fluoro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.65mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.77 g, 6.98 mmol), potassium acetate (1.37 g, 13.95 mmol) and l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (340 mg, 0.46mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (240 mg, 20%): NMR (400 MHz, Chloroform-d) delta 11.44 (m, 1H), 8.73 (d, 7= 1.6 Hz, 1H), 8.46 (d, 7= 1.2 Hz, 1H), 7.10 (m, 1H), 1.39 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-68-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
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Pyridine | C5H5N – PubChem