Pyridine-derivatives

Synthetic Route of 10592-27-5, 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.10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H8N2, molecular weight is 120.15, as common compound, the synthetic route is as follows.

To a solution of sulfurisocyanatidic chloride (22 mg, 0.16 mmol) in DCM (2 mL) was added a solution of Intermediate GW-18.3 (70 mg, 0.15 mmol) and DIPEA (0.05 mL, 0.3 mmol) in DCM (2 mL) in an ice-water bath and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (28.0 mg, 0.233 mmol) in DCM (2 mL) was added, followed by DIPEA (0.11 mL, 0.62 mmol) and the reaction mixture was stirred for 2 min, the bath was removed and the stirring was continuted at rt for 2 h. The reaction mixture was concentrated and purified by preparative HPLC to afford the title compound (19.4 mg). LC-MS retention time = 3.37 min; m/z = 603.20 [M+H]+ (Column: Phenomenex C18 2.0 X 50 mm, 3 muetaiota particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-O. /0 TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

The chemical industry reduces the impact on the environment during synthesis 10592-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84249-14-9, 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.84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

To a solution of 4-bromopyridin-2-amine (5.0 g, 29.07 mmol) in dichloromethane (50 mL) cooled to 0 C was added pyridine (3.5 mL, 43.4 mmol) and the solution was stirred for 10 min. Acetyl chloride (2.1 mL, 29.5 mmol) was added. The reaction mixture was allowed to stir at 0 C for 30 min. Then the reaction mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with brine (50 mL). The aqueous layer was extracted with dichloromethane (3 x 200 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced to afford the title compound (4.1 g, 19.2 mmol, 66%> yield) as a light yellow solid. LCMS (ESI) m/e 215.0 [(M+H)+, calcd for C7H8BrN20, 215.0]; LC/MS retention time (method F): tR = 1.53 min.

Statistics shows that 84249-14-9 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-bromopyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74764-17-3, 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 74764-17-3, name is N1-(Pyridin-2-yl)ethane-1,2-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 6 (3S)-8-Amino-9-fluoro-2,3-dihydro-7-oxo-3-phenylmethyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid A mixture of (3S)-8-Amino-9,10-difluoro-2,3-dihydro-7-oxo-3-phenylmethyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (76.9 mg, 0.207 mmol), 2-(2-pyridylamino)ethylamine (41.8 mg, 0.303 mmol), and triethylamine (42.1 muL, 0.302 mmol) in DMSO (1.5 mL) was stirred at 100 C. for 3 h. The reaction mixture was poured into ice-water and the resulting precipitates were collected by filtration. Recrystallization of the filtered precipitates from CH2Cl2-EtOH gave (3S)-8-amino-9-fluoro-2,3-dihydro-7-oxo-3-phenylmethyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (55.4 mg, 55%) as a yellow powder. 1H NMR (400 MHz, CDCl3) delta 2.98-3.09 (2H, m), 3.71 (2H, br), 3.82 (2H, br), 3.97 (1H, d, J=11.0 Hz), 4.20 (1H, t, J=7.9 Hz), 4.33 (1H, d, J=11.0 Hz), 4.71 (1H, br), 5.75 (1H, br), 6.25 (2H, br), 6.44 (1H, d, J=7.9 Hz), 6.60 (1H, dd, J=6.7, 5.5 Hz), 7.11 (2H, d, J=6.7 Hz), 7.31-7.43 (4H, m), 8.07 (1H, s), 8.69 (1H, dd, J=5.5, 1.5 Hz), 15.1 (1H, s). HRESIMS (+): 490.19342 (calcd for C26H25FN5O4, 490.18906). [alpha]D27-204 (c 0.313, CHCl3).

According to the analysis of related databases, 74764-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cociorva, Oana; Li, Bei; Szardenings, Katrin; Fukuda, Yasumichi; Nomura, Masahiro; Seto, Shigeki; Yumoto, Kazuhiro; Okada, Kyoko; Nakamura, Ayako; US2007/254866; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17282-03-0 ,Some common heterocyclic compound, 17282-03-0, molecular formula is C6H5BrClN, 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.

Synthesis 53 [5-(2-Chloro-5-methyl-pyridi -3-yl)-thiazol-2-yl]-propyl-carbamic acid tert-butyl ester 3-tert-Butyl-1-propyl-1-[5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-thiazol-2-yl]-urea (1 mmol, 0.37 g) 2-chloro-3-bromo-5-methylpyridine (1 mmol, 0.20 g), potassium carbonate (2 mmol, 0.27 g) and bis(triphenylphosphine) palladium(ll)dichloride (0.050 mmol, 0.035 g) were weighed into a microwave vial and treated with dioxane (1.5 mL) and water (0.5 mL). The reaction mixture was heated at 130 C for 15 minutes in a microwave reactor. The reaction mixture was diluted with water (40 mL), extracted with DCM (2×30 mL) and passed through a phase separation cartridge. The organics were evaporated to a brown oil. This was purified by flash column chromatography 1 :9 ethyl acetate cyclohexane to yield the title compound as a pale yellow oil. LCMS, analytical method 2, TR=6.22 mins, 70%, Ml+H=368.

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. 17282-03-0, 3-Bromo-2-chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHARLES, Mark David; BROOKFIELD, Joanna Lola; EKWURU, Chukuemeka Tennyson; STOCKLEY, Martin Lee; WO2015/25172; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22245-83-6, 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 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

5-iodo-3-trifluoromethyl-2-pyridinol C 800C, 2h I>80%[0070] 3-trifluoromethyl-2-pyridinol (25 g, 153.3 mmol) is dissolved in anhydrousCH3CN (150 rnL) and DMF (150 rnL). N-iodosuccinimide (34.5 g, 153 mmol) is then added. The reaction mixture is stirred at 80 0C for 2 hours and cooled to room temperature. Aqueous 1 M NaHCO3 (150 mL) is then added to the cooled mixture. After stirring for 5 min, the solvents are evaporated to dryness. Water is added and the aqueous phase is extracted (x2) with dichloromethane. The organic phase is then evaporated and the desired product is recrystallized in water to afford 36.2 g (81 %) of a white powder.[0071] 1H NMR (500 MHz, CDCl3) delta 7.85 (d, J= 2.3, IH); 7.98 (d, J= 2.3, IH),13.41 (br s, IH); 13C NMR (250 MHz CDCl3) delta 63.0, 121.4 (q, JC-F= 272.3 Hz), 122.2 (q, JC- F= 31.6 Hz), 144.4, 148.1 q, (JC-F= 5.0 Hz), 160.1.

According to the analysis of related databases, 22245-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; WO2008/119015; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14529-54-5, 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. 14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Example 130a 5-Bromo-1-methyl-3-(1-methyl-1H-imidazol-4-ylamino)pyridin-2(1H)-one 130a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (50 mL), 1-methyl-1H-imidazol-4-amine (1.1 g, 11.3 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (3.0 g, 11.3 mmol), Pd2(dba)3 (1.0 g, 1.13 mmol), XantPhos (1.3 g, 2.26 mmol), and cesium carbonate (7.3 g, 22.6 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 92 C. for 4.5 hrs. 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 (100:1 to 50:1) to afford 130a (2.4 g, 76%) as a yellow solid. MS-ESI: [M+H]+ 283.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1072-97-5, 5-Bromopyridin-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, 1072-97-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 4 Preparation of compound 8: 1. An ethanol solution of compound 5 (12400 g in 51 L of ethanol) was added to an appropriately sized stainless steel reactor at room temperature under nitrogen atmosphere. 2. Compound 6 (9500 g) was added as a solid in one portion at room temperature. 3. The reaction mixture was heated to reflux (?78C) and stirred for 1-2 days. 4. The reaction was monitored by HPLC. 5. Upon completion, the reaction mixture was allowed to cool to room temperature. 6. NaOH solution (9884 g solid pellets dissolved in 38 L of water) was added as a stream over a 30 min period at an internal temperature below 35 C. 7. The reaction mixture was heated to reflux (?78C) for 3 to 4 hours. 8. The reaction was monitored by HPLC. 9. Upon completion, the reaction mixture was cooled to an appropriate temperature to start solvent removal. 10. All ethanol (approximately 5 volumes of ethanol) was removed under vacuum at 40 to 45 C. 11. The reaction mixture was cooled to room temperature. 12. Water (57 L; 6 vol) was added at room temperature. 13. The aqueous solution was washed with ethyl acetate (2 x 38 L) to remove all organic impurities. 14. The lower aqueous layer was cooled to 0-5 C and acidified with cone. HCl (?15 L) until reaching pH 1-2. 15. The reaction mixture was stirred for 1 to 2 hours at 0 to 5 C. 16. The mixturewas filtered and the cake was washed with water (2 x 38 L) and acetone (2 x 19L) followed by drying for 1-2 hours. 17. The solid collectedwas transferred back into an appropriately sized reactor. 18. Heptane (95 L; 10 vol) was addedto the reactor; the suspension was stirred for 4 to 5 hours at roomtemperature. 19. The solidwas collected by filtration and washed with heptane (2 x 19 L). 20. The solid (15 kg) was suspended in methanol (75 L; 5 vol) at room temperature for 2 hours. 21. The suspension was filtered and the solid collected was washed with methanol (2x 5L). 22. The solid was dried under vacuum at 50C to constant weight to give compound 8 as an off-white to white solid (10169 g, 83.3 % yield; HPLC purity 99.2%;1HNMR (DMSO-d6, 300 MHz) delta 9.4 (s, 1H), 8.3 (s, 1H), 7.85-7.67 (m, 2H)).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-97-5, its application will become more common.

Reference:
Patent; IP Gesellschaft fuer Management mbH; Trinius, Frank; EP2792360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 209328-55-2, 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 209328-55-2, name is 5-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows.

Nitric acid (0.25 mL, 5.0 mmol) was added over 1 min to a solution of 5-fluoropyridin-3-ol (0.25 g, 2.2 mmol) and sulfuric acid (3 mL) at 70 C. After 20 min, a second aliquot (0.25 mL) of nitric acid was added over 1 min. After an additional 40 min, the reaction was cooled to 0 C. Water (25 mL) was added followed by slow addition of 10 N NAOH (13 mL) at 0 C. The solution was neutralized with 1 N HCI and concentrated to give 5-FLUORO-2-NITROPYRIDIN-3-OL. MS (ESI): 158. 8 (M+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 209328-55-2, 5-Fluoropyridin-3-ol.

Reference:
Patent; MERCK & CO., INC.; WO2005/21529; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,3-Dichloro-5-(trifluoromethyl)pyridine

1.82 kg of 3-chloro-2-chloro-5-trifluoromethylpyridine was dissolved in 27.231 L of methanol,Then 1.0119 kg of triethylamine was added thereto,Heated to reflux for 4 hours, and cooled to 20 C to obtain a reaction solution,The resulting reaction solution was filtered to obtain a filter cake,The resulting filter cake was vacuum dried at 40 C for 1 hour to obtain an organic salt; The organic salt obtained in step (1), 0.27 kg of hydrocyanic acid was added to 2.7 L of dichloromethane and 1.35 L of water,The reaction was stirred at 0 C for 3 hours to obtain a mixed solution, and the resulting mixture was allowed to stand at room temperature to obtain an organic phase a;The obtained organic phase a is added to hydrochloric acid to adjust its pH to 2 and then the layers are separated to obtain an acid water layer and an organic layer,The resulting organic layer was washed with water to a pH of 6 to give the washed water and the organic phase b; The organic phase b obtained in step is distilled at atmospheric pressure to 60 C and then distilled under reduced pressure,Collection of vacuum 2mmHg,The temperature of the ketone temperature of 70 to 120 C is 1.77 kg of 3-chloro-2-cyano-5-trifluoromethylpyridine,Yield 85.7%.

With the rapid development of chemical substances, we look forward to future research findings about 69045-84-7.

Reference:
Patent; Shandong Province Union Pesticide Industry Co., Ltd; Tang, Jianfeng; Pan, Guangmin; Li, Wenhong; Su, Jingchi; Zhao, Baoxiu; Liu, Jie; (9 pag.)CN106349159; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15471-17-7, 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 15471-17-7, name is 3-(Pyridin-1-ium-1-yl)propane-1-sulfonate. This compound has unique chemical properties. The synthetic route is as follows.

Please refer to FIG. 2 and FIG. 3, which are a view showing reactions of fabricating the IL; and a view showing transacylation and stratification. As shown in the figures, on using the present invention, for fabricating an acidic IL as a catalyst, pyridine or 1-butyl-imidazole (N-butyl imidazole) is reacted with 1,3-propane sultone at 40 C. for 24 hrs to obtain a white solid of a zwitterionic compound. After being purified with ether and dried through vacuuming, the white solid of the zwitterionic compound of R+-(CH2)3-SO3- is obtained, where R is pyridine or 1-butyl-imidazole (i.e. n-propane sulfonic acid pyridinium (PSPy) or pyridinium propyl sulfobetaine (PPS)). An appropriate amount of the white solid is obtained in a round bottom flask to be added with a considerable number of moles of sulfuric acid for reaction with stirring at 100 C. for 0.5 hr. A transparent viscous liquid is gradually formed, which is an acidic IL of [R+-(CH2)3-SO3H][HSO4] obtained through the reaction shown in FIG. 2.

According to the analysis of related databases, 15471-17-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CPC CORPORATION, TAIWAN; Wu, Jung-Chung; Huang, Ming-Yu; Lin, Jann-Chen; Wang, Yih-Ping; (11 pag.)US9586886; (2017); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem