Day: March 24, 2022

Synthetic Route of 1201676-03-0 ,Some common heterocyclic compound, 1201676-03-0, molecular formula is C7H4Cl2N2O, 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.

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (0.655 g, 3.23 mmol), triethylamine (2.61 g, 25.8 mmol), and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3- a]pyrazine hydrochloride (0.544 g, 3.39 mmol) in dioxane (7.5 ml.) is stirred in a 48 ml_ sealed tube at 12O0C for 16 h. Additional 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine hydrochloride (0.500 g, 3.11 mmol) is added to the mixture, which is heated again at 12O0C for 24 h. A light yellow powder is isolated by filtration of the room temperature reaction mixture (0.61 1 g, 2.10 mmol, 65%). MS(ESI) m/z 291.18 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.1 1 (s, 1 H), 8.50 (s, 1 H), 7.01 (s, 1 H), 4.97 (s, 2 H), 4.68 (s, 2 H), 4.19 (t, J=5.31 Hz, 2 H), 4.01 (t, J=5.43 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1201676-03-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77199-09-8, 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.77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

To a solution of 27 (20.0 g, 86.9 mmol) in DMF (100 mL) wereadded tributyl(vinyl)tin (28.1 mL, 95.6 mmol) and Pd(PPh3)4 (2.01 g, 1.74 mmol), and the mixture was stirred at 100 C for 2 hunder Ar atmosphere. The mixture was diluted with water(200 mL), and extracted with AcOEt (400 mL). The extracts werecombined, washed with brine (200 mL), dried over Na2SO4 andconcentrated in vacuo. The residue was purified by silica gel columnchromatography (hexane/AcOEt = 49/1 to 4/1) to give ethyl5-ethenylpyridine-2-carboxylate (16.5 g, quant.) as pale yellowoil. To a solution of obtained compound above (7.71 g, 43.5 mmol)in EtOH (77 mL) was added 10% Pd-C (1.54 g) and the mixture wasstirred at room temperature for 3 h under H2 atmosphere. The mixturewas filtered through membrane filter, and the filtrate was concentratedin vacuo to give the title compound (7.92 g, quant.) aspale yellow oil. 1H NMR (DMSO-d6) d 1.22 (3H, t, J = 7.6 Hz), 1.33(3H, t, J = 7.1 Hz), 2.71 (2H, q, J = 7.6 Hz), 4.33 (2H, q, J = 7.1 Hz),7.83 (1H, dd, J = 8.0, 2.2 Hz), 7.98 (1H, d, J = 8.0 Hz), 8.58 (1H, d,J = 2.2 Hz).

Statistics shows that 77199-09-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-bromopicolinate.

Reference:
Article; Ohashi, Tomohiro; Tanaka, Yuta; Shiokawa, Zenyu; Banno, Hiroshi; Tanaka, Toshio; Shibata, Sachio; Satoh, Yoshihiko; Yamakawa, Hiroko; Yamamoto, Yukiko; Hattori, Harumi; Kondo, Shigeru; Miyamoto, Maki; Tojo, Hideaki; Baba, Atsuo; Sasaki, Satoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4777 – 4791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74936-72-4, 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 74936-72-4 as follows.

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylic acid (700g, 2.1mol) in methanol (14 L) was added Quinidine (617g, 1.90mol). The mixture was stirred at 90C under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl -4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74936-72-4, its application will become more common.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 637348-81-3, 3-Bromo-5-iodopyridin-2-ol, 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, Product Details of 637348-81-3, blongs to pyridine-derivatives compound. Product Details of 637348-81-3

Example 214b 3-Bromo-5-iodo-1-methylpyridin-2(1H)-one 214b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 214a (6.0 g, 20.0 mmol), iodomethane (4.26 g, 30.0 mmol), and K2CO3 (5.52 g, 40.0 mmol). The mixture was stirred at room temperature for 2 h and diluted with water (200 mL). The resulting white solid was collected by filtration to afford 214b (5.97 g, 95%) as a white solid. MS-ESI: [M+H]+ 314

At the same time, in my other blogs, there are other synthetic methods of this type of compound,637348-81-3, 3-Bromo-5-iodopyridin-2-ol, and friends who are interested can also refer to it.

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

Adding a certain compound to certain chemical reactions, such as: 60781-83-1, 4-Phenylpyridin-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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Add tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium t-butoxide (52.7 g, 549 mmol) to 1-3 (30.83) A solution of g, 80.44 mmol) and 1-4 (13.69 g, 80.44 mmol) in degassed toluene (500 mL), and the mixture was heated under reflux for 2 hours.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc.The filtrate was diluted with water and extracted with toluene and the organic phases were combined and evaporated in vacuo. The residue was filtered through silica gel (heptane / dichloromethane) and crystallised from isopropyl alcohol.Intermediate 1-5 38.43 g was obtained in a yield of 81.32%.

The synthetic route of 60781-83-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhang Hong; Cai Hui; (28 pag.)CN108440524; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109306-86-7, 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. 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

General procedure: Process (i) A dry 50-mL two-necked round bottom flask equipped with a glass stopper and a three-way stopcock was charged with 2-(2-chlorophenyl)pyridine (1.20 g, 6.32mmol) and CH2Cl2 (10 mL). The resulting colorless solution was cooled to 0 C, and mCPBA (1.64 g, 9.50mmol) was added slowly. The temperature was gradually raised to rt, and the colorless solution was stirred for 6 h. Cooling again to 0 C, 1M aq NaOH (10 mL) was slowly added. The organic layer was washed with 1M aq NaOH (10 mL) and brine (10 mL), and then dried over Na2SO4 (10 g). Filtration followed by evaporation gave nearly pure 2-(2-chlorophenyl)-pyridine-N-oxide (1.28 g) as a yellow oil. This was used for the next reaction without further purification.

According to the analysis of related databases, 109306-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Shinji; Suzuki, Yusuke; Kimura, Takahiro; Kitamura, Masato; Bulletin of the Chemical Society of Japan; vol. 92; 10; (2019); p. 1707 – 1720;,
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. 477871-32-2, name is 6-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C6H4BrN3

5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-3-iodopyridin-2-amine The mixture of 6-amino-5-bromonicotinonitrile (3.315 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq), and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq) in anhydrous dioxane (40 mL under nitrogen atmosphere was stirred at 120 C. for 20 hours. The mixture was cooled to room temperature then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the crude solid residue was subject to a column chromatography started first with EtOAc-Hex (1:5 to 1:1) followed by MeOH-CHCl3 (1:100 to 1:20). Product containing fractions were all collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:4) yielding 3-iodo-5-isocyanopyridin-2-amine as an off-white solid in the amount of 2.75 g upon filtration. 1H NMR (600 MHz, DMSO-d6) delta ppm 8.35 (d, J=1.76 Hz, 1H) 8.30 (d, J=1.76 Hz, 1H) 7.14 (br. s., 2H).

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, 477871-32-2, 6-Amino-5-bromonicotinonitrile.

Reference:
Patent; Allergan, Inc.; Boral, Sougato; Malone, Thomas C.; Wang, Shimiao; Rao, Sandhya; Yang, Rong; (28 pag.)US2016/102081; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89640-55-1, 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. 89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, 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.

To the reaction mixture containing Intermediate IB (31.8 mg, 0.1 mmol) was added 3-iodo-4-methoxypyridine (125.5 mg, 0.534 mmol), sodium carbonate (68.1 mg, 0.643 mmol) and EtOH:DME:H20 (1.2:2.5: 1.0 ratio) (1.5 mL). The reaction mixture was purged with argon, then treated with tetrakis(triphenylphosphine)palladium (0) (23 mg, 0.020 mmol). The reaction mixture was purged with argon again, securely capped, and placed in a 105C oil bath for 2 h 45 min. The reaction mixture was cooled to room temperature, then diluted with DMF (4 mL). The resulting solution was filtered through a 0.45 uM frit attached to a single-use Waters C-18 sep-pak light cartridge (part No.WAT023501), and then purified by preparative HPLC (Condition A) using aPhenomenex Luna Axia 30 x 100 mm S10 column from 20% Solvent B to 85% Solvent B over 12 min, ret. T = 4.84 min to afford the title compound (12 mg, 31%) as a white solid. ¾ NMR (500 MHz, DMSO-d6) delta ppm 3.91-3.97 (m, 3 H), 4.04 (d, J=7.93 Hz, 2 H), 7.35 (d, J=3.36 Hz, 1 H), 7.49-7.58 (m, 1 H), 7.79-7.86 (m, 2 H), 8.40-8.47 (m, 1 H), 8.59-8.68 (m, 3 H), 8.78-8.85 (m, 2 H). LC/MS (Condition B): ret. T = 2.0min, (M+H)+ 382.04. Analytical HPLC: (Condition A): >97%, ret. T = 16.13 min, (Condition B):>97%, ret. T = 18.28 min, (Condition C): >98%, ret. T = 5.96 min, (Condition D): >98%, ret. T = 6.61 min.

According to the analysis of related databases, 89640-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127406-55-7, 4-Pyridin-3-yl-benzaldehyde, 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, 127406-55-7, blongs to pyridine-derivatives compound. Recommanded Product: 127406-55-7

Methyl iodide (0. 8 ml, 12. 9 mmol) was added to a solution of 4- (3-PYRIDYL) benzaldehyde (0. 78 g, 4. 3 mmol) in dichloromethane and stirred 2 days. Additional methyl iodide (0. 8 ml, 12. 9 mmol) was added and stirred for 3 hr. After removal of the solvent, methanol was added to the residue and ice-cooled. Sodium tetrahydroborate (6. 4 g, 17. 0 mmol) was added to the solution and stirred for 1. 5 hr with warming to room temperature. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. After removal of the solvent under reduced pressure, residue was purified by silica gel chromatography (eluent ethyl acetate to methanol) to give 3-(4-HYDROXYMETHYLPHENYL)-1-METHYL-1, 2, 5, 6- TETRAHYDROPYRIDINE (0. 63 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127406-55-7, its application will become more common.

Reference:
Patent; MITSUBISHI PHARMA CORPORATION; SANOFI-SYNTHELABO; WO2004/85408; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936011-17-5 ,Some common heterocyclic compound, 936011-17-5, molecular formula is C7H6BrNO2, 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 60b (20.5 g, 0.095 mol)was dissolved in THF (400 mL) the resulting solution was stirred at 0C under N2 then treated with LiAlH4 (3.9 g 0.1 mol), maintained the temp below 10C, After addition ,the colorless solution turned to purplish red and stirred at r.t. for 2hrs.TLC showed Compound 232 was consumed, water (4 mL) 15% NaOH (4 mL) and water (12 mL) was added successively the mixture was stirred at r.t for lhr, Na2S04 (50 g) was added, the suspension was filtered off and washed with EA (200 mL), the filtrate was concentrated to give the desired product (Example 60c, 9.4 g, yield 93%) as a brown oil. LCMS [M+H]+=218, 220.

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. 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem