Month: July 2021

Electric Literature of 75806-84-7 ,Some common heterocyclic compound, 75806-84-7, molecular formula is C6H2BrClF3N, 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.

Preparation Example 1 Ten grams of 2-bromo-3-chloro-5-trifluoromethylpyridine was dissolved in 100 ml of dry diethyl ether in a nitrogen stream, and the resulting solution was cooled to -78 C. To the solution thus cooled was gradually dropwise added 30 ml of a 15% solution of n-butyl lithium in hexane, and the resulting mixture was stirred at that temperature for 30 minutes. Thereafter, an excessive amount of pulverized dry ice was gradually introduced into the solution. The temperature of the solution was returned to room temperature, and the solution was stirred at that temperature for an additional 1 hour. After the reaction was completed, 100 ml of water was added to thereby subject to the extraction. An aqueous layer thus formed was isolated and made acidic by adding thereto concentrated hydrochloric acid to form an oily product. The thus formed oily product was extracted with 300 ml of methylene chloride. After drying an organic layer over anhydrous sodium sulfate, the solvent was evaporated off under reduced pressure to obtain 5.1 g of 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-84-7, its application will become more common.

Reference:
Patent; Ishihara Sangyo Kaisha, Ltd.; US4367336; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15506-18-0, 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

[0625] To a solution of 2-(4-(2,4-difluorophenoxy)piperidin-l-yl)-5- (etaiotaomicronphi1etaomicron8Homicronetanu1)rhonupieta-3-3etapietaepsilon (50.00 mg, 1 10.0 muiotaetaomicron, 1.00 eq) and 1 -methyl -2 -oxo- 1,2- dihydropyridine-3-carboxylic acid (20.22 mg, 132.0 mutauetaomicron, 1.20 eq) in DMF (2 mL) was added HATU (62.75 mg, 165,02 muiotaetaomicron, 1.50 eq) and DIPEA (42.65 mg, 330.0 muetaiotaomicron, 57.64 mu,, 3.00 eq). The resulting mixture was stirred at 25C for 12 hours, then diluted with EtOAc (50 mL) and washed with saturated aq N’a >(*<) > (20 rnL) and brine (20 mL). The organic layers were dried over anhydrous NazSC filtered, concentrated in vacuo, and purified by preparative HPLC (basic mode) to give the title compound as a white solid (18 mg, 27%). .H NMR (400 MHz, CDCb) delta ppm 2.09 – 2.27 (m, 4 H), 3.01 – 3.15 (m, 4 H), 3.15 – 3.24 (m, 2 H), 3.54 – 3.63 (m, 2 H), 3.72 (s, 3 H), 3.75 – 3.85 (m, 4 H), 4.42 (dt,./ 7. 1. 3.5 Hz, 1H), 6.49 (t,./ 7. 1Hz, 1H), 6.74 – 6,83 (m, 1 I D. 6.87 (ddd, J=l 1.0, 8.4, 3.1Hz, 1H), 7.03 (td,,7=9.2, 5.5 Hz, 1H), 7.64 (dd, J=6.6, 1.8 Hz, 1H), 8.43 (d, J=2.2 Hz, 1H), 8.60 (dd, J=7.3, 2.0 Hz, 1H), 9.07 (d, J=2.2 Hz, 1H), 12.23 (s, 1H); ESI-MS m/z] M · Pi | 590.0.

The synthetic route of 15506-18-0 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

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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, 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 (2-Aminopyridin-4-yl)methanol

To a stirred solution of 67 (1.39 g, 11.2 mmol) in EtOH (46.5 ml)-water (6.5 ml) was added NaHCO3 (1.88 g, 22.3 mmol), followed by a 50percent w/w aqueous solution of chloroacetaldehyde (2.84 ml, 1.75 g, 22.4 mmol). The resultant suspension was stirred and refluxed for 2 h. The dark amber-colored reaction mixture was carefully concentrated (frothing) under reduced pressure to approximately half its original volume and then filtered. Collected solid was washed with MeOH. Combined filtrate and washings were concentrated in vacuo and yielded a dark, oily two-phase mixture. Treatment with EtOH produced a mixture of solid precipitate and a homogeneous liquid phase, which was filtered. The filtrate was concentrated under reduced pressure to a dark oil, which was purified via flash chromatography on silica gel, eluting with CH2CI2-CH3OH -NH4OH (91.5:8.5:0.25), to obtain compound 68 as a pale yellow solid (1.34 g; 80percent). To a solution of 68 (1.20 g, 8.10 mmol) in MeOH (5 ml) was added acetone (48 ml). A small amount of dark precipitate formed and was removed by filtration (0.45 muM syringe filter). To the clear yellow filtrate was added via syringe 1 M ethereal HCI (8.1 ml, 8.1 mmol). The resultant mixture was stirred briefly and was then filtered. The hygroscopic solid thus isolated was washed rapidly with acetone and dried under vacuum at 50 0C to obtain the hydrochloride salt of 68 as a tan powder (1.34 g; 89percent). EPO

With the rapid development of chemical substances, we look forward to future research findings about 105250-17-7.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 686279-09-4, Ethyl 4,6-dichloro-2-methylnicotinate, 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, SDS of cas: 686279-09-4, blongs to pyridine-derivatives compound. SDS of cas: 686279-09-4

THF (52.3 mL) was cooled to 0C in a dry round bottomed flask under an atmosphere of N2 gas. Ethyl 4,6-dichloro-2-methylnicotinate (4.60 mL, 26.1 mmol) was then added followed by diisobutylaluminum hydride (57.5 mL, 57.5 mmol). The reaction was stirred at 0C for 3 h. The reaction was then poured into cold saturated sodium potassium tartrate solution. The mixture was stirred for several hours to allow the precipitate to dissolve, then the aqueous phase was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0-50% EtOAc/hexanes) to give (4,6-dichloro-2-methylpyridin-3-yl)methanol. MS ESI calc’d. for C7H8C12N0 [M+l]+ 192, found 192.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,686279-09-4, Ethyl 4,6-dichloro-2-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIPFORD, Kathryn; FALCONE, Danielle; SLOMAN, David, L.; WITTER, David, J.; WO2015/94929; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211540-74-7, 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.1211540-74-7, name is Ethyl 2-(5-bromo-3-nitropyridin-2-yl)acetate, molecular formula is C9H9BrN2O4, molecular weight is 289.08, as common compound, the synthetic route is as follows.

To a solution of Intermediate 88 (10.0 g, 34.6 mmol) in acetic acid (200 mL) wasadded iron (9 .51 g, 173 mmol). The reaction mixture was stirred at 60C for 4 h, then10 diluted with EtOAc (200 mL ), stirred for 15 minutes, filtered through a pad of Celite, andwashed with EtOAc (3 x 200 mL). The organic layer was separated, dried overanhydrous NazS04 and concentrated in vacuo. The crude residue was dissolved in 5%MeOH in EtOAc (30 mL) and adsorbed onto Fluorosil. The resulting slurry was filteredthrough a Celite pad and washed with 5% MeOH in EtOAc (3 x 200 mL). The organic15 layer was dried over anhydrous NazS04 and concentrated in vacuo, to afford the titlecompound (5.00 g, 68%) as a brown solid. DH (400 MHz, DMSO-d6) 3.57 (s, 2H), 7.30(s, IH), 8.17 (s, IH), 10.67 (br s, IH). HPLC-MS (method 6): MH+ m/z 213.0, RT 1.31minutes.

Statistics shows that 1211540-74-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-(5-bromo-3-nitropyridin-2-yl)acetate.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13603-44-6, Adding some certain compound to certain chemical reactions, such as: 13603-44-6, name is 2,6-Dimethylpyridin-4-ol,molecular formula is C7H9NO, 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 13603-44-6.

Example 121: 2-(4-chloro-3-fluorophenoxy)-A^-(3-{2-[(2,6-dimethylpyridin-4- yl)oxy]acetamido}bicyclo[l.l.l]pentan-l-yl)acetamide (Compound 220) A mixture of Example 28A (65.0 mg, 0.180 mmol), 2,6-dimethylpyridin-4-ol (33.2 mg, 0.270 mmol), potassium carbonate (49.7 mg, 0.360 mmol), and potassium iodide (2.091 mg, 0.013 mmol) in acetone (2.5 mL) was heated at 140 C in a Biotage Initiator microwave reactor for 40 minutes. The reaction mixture was concentrated. The residue was treated with brine and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by HPLC (see protocol in Example 112D) to provide the title compound as a trifluoroacetic acid salt (53.2 mg, 53%). XH NMR (400 MHz, DMSO-c) delta ppm 8.88 (s, 1H), 8.72 (s, 1H), 7.47 (t, J = 8.9 Hz, 1H), 7.26 (s, 2H), 7.05 (dd, J = 11.4, 2.9 Hz, 1H), 6.83 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.79 (s, 2H), 4.46 (s, 2H), 2.57 (s, 6H), 2.25 (s, 6H). MS (ESI+) m/z 448.1 (M+H)+.

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. 13603-44-6, 2,6-Dimethylpyridin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farath; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (445 pag.)WO2017/193034; (2017); A1;,
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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F3N2O3, 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. Recommanded Product: 33252-64-1

(2) 52g of compound 2 was added to 150ml of phosphorus oxychloride,With stirring slowly add 21g of quinoline,Control feeding speed,So that the internal temperature does not exceed 50 degrees,At the same time compound 2 slowly dissolved,Argon gas protection system, oil bath heating,Set the external temperature 120 degrees,20-30 minutes after the system began to reflow,Maintain the system slightly boiled for 1.5 hours.TLC showed the reaction of raw materials is completed, stop heating,The system was concentrated under reduced pressure to remove phosphorus oxychloride, then dissolved in EA (400 ml) and the quinoline was removed by washing with 2N HCl (200 ml * 2)The mixture was washed with saturated sodium bicarbonate solution to neutrality and the organic phase was dried to give compound 3.TLC information: Raw material Rf = 0.1,Product Rf = 0.7. Developing agent: PE / EA / = 15/1.Measured product 50 grams, brown oil, yield 88%

With the rapid development of chemical substances, we look forward to future research findings about 33252-64-1.

Reference:
Patent; Si Fenke Si Pharmaceutical Research And Development (Tianjin) Co., Ltd.; Yao Qingjia; Li Changyong; Xu Yangjun; (8 pag.)CN105111209; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1231930-25-8 , The common heterocyclic compound, 1231930-25-8, name is 1-((6-Bromopyridin-3-yl)methyl)-4-ethylpiperazine, molecular formula is C12H18BrN3, 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 5-(2-aminopyrimidin-4-yl)-N-cyclopentyl-4-rnethylthiazol-2-amine (275 mg, 1.00 rnmol) in dioxane (3 mL) were added i-((6-bromopyridin-3-yl)methyl)-4-ethylpiperazine (341 mg,1.2 rnrnol), Pd2dba3 (45.8 mg, 0.05 rnrnol), xantphose (58 mg, 0.1 rnrnol) and t- BuONa (144 mg, 1.5 mmol) and heated under microwave irradiation at 150 C for 1 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, DCM ramping to DCM:MeOH:NH4OH = 9: 1:0.3) and recrystallised with DCM and MeOH to give 83 as a white solid (200 mg, 42%). 1H NMR (CDC13) 1.09 (t, 3H, .17.0), 1.58 – 1.76 (m, 6H), 2.08 – 2.14 (in, 2H), 2.43 (q, 2H,J7.0, CH2CH3), 2.55 (s br, I IH), 3.48 (s, 2H), 3.86-3.92 (in, 1H), 5.42 (d, 2H,,J7.0), 6.90(d, IH,,15.5), 7.68 (dd, lH,,19.() & 2.5), 7.89 (s, 1H), 8.19 (d, 1H,J2.0), 8.35-8.38 (in, 2H). HRMS (ES1): m/z 479.2703M+H] calcd. for C75H35N8S [M+HV 47c.2700. Anal. RP-HPLC Method A: 1R 9.89 mm, purity> 96%; Method B: ?R 8.66 mm, purity> 96%.

The synthetic route of 1231930-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF SOUTH AUSTRALIA; WANG, Shudong; ZELEKE, Solomon Tadesse; YU, Mingfeng; (90 pag.)WO2017/20065; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67443-38-3, 5-Bromo-2-chloro-3-nitropyridine, 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, 67443-38-3, blongs to pyridine-derivatives compound. HPLC of Formula: C5H2BrClN2O2

63a (3 g, 1.0 eq) is dissolved in THF (13 mL), and then cooled to 0 C. Methylamine solution (2M in THF, 20.8 mL, 3.3 eq), is slowly added to the reaction mixture (exothermic). The reaction mixture is stirred for 30 min at 0 C. and diluted with EtOAc. Organic layer is washed with sat aq sodium bicarbonate. The aqueous layer is re-extracted with EtOAc (2×). The organic phase is washed with brine, dried with MgSO4, filtered and concentrated under reduced pressure to obtain 63b which dried under high vacuum for 16 h (2.95 g, quantative yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67443-38-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/261714; (2010); A1;,
Pyridine – Wikipedia,
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. 1053655-66-5, name is 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine

To the solution of compound 6-bromo-[l,2,4]triazolo[l,5-a]pyridine (0.2 g, 1 mmol), trimethyl borate (0.12g , 1.2 mmol) in toluene and THF (50 mL,V/V=4:l) was added /-BuLi (1.2 mL, 1.2 mmol, 1.0 M in hexane) at -780C. The reaction mixture was stirred for 1 h at -780C, then the reaction mixture was warmed to -150C and quenched with 2 N HCl (1 mL, 2 mol). The mixture was concentrated. Purification by chromatography (MeOH: DCM = 1 : 10) afforded [l,2,4]triazolo[l,5-a]pyridin-6-ylboronic acid (O. lOg, 55%) as light yellow solid. MS (m/z) (Mf+H): 164.

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, 1053655-66-5, 7-Bromo-[1,2,4]triazolo[1,5-a]pyridine.

Reference:
Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem