Day: April 21, 2022

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. 1721-23-9, name is 3-Cyano-2-methylpyridine, molecular formula is C7H6N2, 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. Application In Synthesis of 3-Cyano-2-methylpyridine

Step 3 Preparation of 2-methyl-3-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine: To a suspension of 4-(methylsulfonyl)aniline hydrochloride (6.85 g, 0.040 mol) in dichloroethane (400 mL) was added triethylaluminum (1.9M solution in toluene, 32.0 mL, 60 mmol) over 15 minutes at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 3-cyano-2-methylpyridine, from step 2, in 70 mL of dichloroethane was added over 10 minutes and the mixture was stirred at 75 C. for 16 hours. The reaction mixture was cooled to room temperature and treated with 50 g of silica gel. The mixture was stirred for 30 minutes and filtered. The filtrate and washings were concentrated under reduced pressure and the residue was washed with ether to give 7.3 g of crude 2-methyl-N-[4-(methylsulfonyl)phenyl]-3-pyridinecarboximidamide (60%). To a mixture of the above crude amidine (7.0 g, 0.024 mol) and sodium bicarbonate (4;0 g, 0.048 mol) in isopropanol (350 mL) was added 3-bromo-1,1,1-trifluoroacetone (6.9 g, 0.036 mol) rapidly at room temperature. After heating the reaction mixture at 75-80 C. for 16 hours, the solvent was removed and the residue was partitioned between water and methylene chloride. The organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (ethyl acetate/acetone, 98:2) to give 4.02 g of pure 2-methyl-3-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine as a yellow solid (25%): mp (DSC) 237-239 C. Anal. Calc’d. for C17 H16 F3 N3 O3 S: C, 51.12, H, 4.04, N, 10.52, S, 8.03. Found: C, 50.92, H, 4.12, N, 10.04, S, 7.83.

With the rapid development of chemical substances, we look forward to future research findings about 1721-23-9.

Reference:
Patent; GD Searle & Co; US5616601; (1997); A;,
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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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. Formula: C8H8BrNO2

Under the protection of N2, m-chloroperoxybenzoic acid (36.00g, 0.208 mol) was added to an ethyl acetate (126 mL) solution of ethyl 5-bromopyridine-2-carboxylate (15.00g, 0.065 mol), and the resulting mixture was heated to 70C to react overnight. After cooling, water was added. The resulting mixture was extracted with ethyl acetate, washed with a saturated sodium sulfite aqueous solution, washed with a saturated sodium carbonate aqueous solution, dried with anhydrous sodium sulfate, and concentrated. The residue was separated through a silica gel column (ethyl acetate:petroleum ether=1:5) to obtain a yellow product (6.60 g, 41%). 1H NMR (400 MHz, CDCl3,) delta 8.42 (d, 1H), 7.53 (d, 1H), 7.41-7.43 (m, 1H), 4.44-4.50 (q, 2H), 1.42 (t, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 77199-09-8.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 40381-92-8, name is 2,5,6-Trichloronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6HCl3N2

[0535] A solution of 2,5,6-trichloronicotinonitrile (30 g, 144.92 mmol, 1.00 equiv) in sulfuric acid (98%, 162 mL, 1.00 equiv) was stirred for 1 h at 60 C in an oil bath. The reaction mixture was cooled and then quenched by the addition of water/ice. The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 26 g of 2, 5, 6-trichloronicotinamide as a white solid. LC-MS (ES, m/z): 225 [M+H]+. 1H-NMR (300MHz, DMSO-<¾) delta (ppm) 9.38 (1H, s), 8.12 (1H, s), 7.95 (1H, s). 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, 40381-92-8, 2,5,6-Trichloronicotinonitrile. Reference:
Patent; ANACOR PHARMACEUTICALS, INC; JARNAGIN, Kurt; AKAMA, Tsutomu; WO2011/94450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116308-35-1, 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 116308-35-1 as follows.

A solution of 2-(trifluoromethyl)nicotinaldehyde (1.96 g, 11.19 mmol) and hydroxylamine hydrochloride (0.856 g, 12.31 mmol) in pyridine (6 mL) was stirred at rt for 1 h. Pyridine was removed under vacuum to give the desired product (2.12 g, 100%) as a white solid: LCMS (ES): m/z 191.0 [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,116308-35-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FENG, Jianxin; LIU, Chunjian; HUANG, Yanting; (130 pag.)WO2019/89665; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

2,6-Dibromo-4-methylpyridine (D2, 1.279g, 5.098mmol) was dissolved in anhydrous dimethylsulfoxide (12ml) and stirred at room temperature. Hydrazine monohydrate (0.99ml, 20.39mmol, 4eq.) was added slowly and the mixture was then stirred at room temperature for 3 hours and then at 12O0C for 18 hours. The mixture was cooled to room temperature and poured into water and the resulting precipitate was collected by filtration, washed with water and dried to give the title compound (881 mg, 85%) as a beige coloured solid. LCMS (method A): major peak, Rt = 1.60mins; MH+ 202, 204.

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/68652; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89402-42-6 , The common heterocyclic compound, 89402-42-6, name is 2,3-Difluoro-5-(trifluoromethyl)pyridine, molecular formula is C6H2F5N, 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 3-Fluoro-2-phenylthio-5-trifluoromethylpyridine Over a period of 2.5 h, 59.6 g (0.326 mol) of 2,3-difluoro-5-trifluoromethylpyridine were added at 148-156 C. to 37.7 g (0.338 mol) of 98.7% pure thiophenol and 2.1 mg (0.01 mol %) of copper powder, and the mixture was stirred at 156-164 C. for 2 hours. After cooling, the residue was taken up in methylene chloride, washed with 0.5 N of aqueous sodium hydroxide solution and with water, dried over magnesium sulfate and concentrated under reduced pressure. 88.9 g (100% of theory) of the title compound of n24/D=1.5539 were obtained.

The synthetic route of 89402-42-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US6420314; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60289-67-0, 1-(Pyridin-3-yl)propan-1-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, SDS of cas: 60289-67-0, blongs to pyridine-derivatives compound. SDS of cas: 60289-67-0

Example 18 N-(1-Pyridin-3-yl-propyl)-2-(quinoline-8-sulfonylamino)-benzamide The title compound was obtained from 2-(quinoline-8-sulfonylamino)-benzoyl chloride (example 1b) and 1-pyridin-3-ylpropylamine (precursor 3n). MS (ES): 447 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60289-67-0, 1-(Pyridin-3-yl)propan-1-amine, and friends who are interested can also refer to it.

Reference:
Patent; Brendel, Joachim; Bohme, Thomas; Peukert, Stefan; Kleemann, Heinz-Werner; US2003/114499; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1193-71-1, 4,6-Dimethylpyridin-3-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, 1193-71-1, blongs to pyridine-derivatives compound. SDS of cas: 1193-71-1

A solution of step 1 intermediate of example 14 (301 mg, 951 pmol) in thionyl chloride (3 mL) was heated to 70 C for 4 h. The volatiles were removed under reduced pressure and the residude was dissolved in CH2CI2 (14 mL) and NEt3 (254 pL, 1.79 mmol) and 4,6-dimethylpyridine-3-amine (114 mg, 940 pmol) were consecutively added and the mixture was stirred at rt overnight. The volatiles were removed underreduced pressure and the residue was purified by chromatography (lnterchim cartridge 5OSiHP /12 g,EtOAc/Cy) to yield the title compound of example 19 (136 mg, 36%).LC-MS (Method 2): m/z [Mi-H] = 421.1 (MW calc. = 420.80); R = 0.59 mm.1H-NMR (DMSO-d6): 6 = 9.84 (s, 1H), 8.36 (s, 1H), 7.93 (s, IH), 7.73 (s, 1H), 7.17 (s, 1H), 6.85 (s, 1H),3.77 (s, 3H), 2.43 (s, 3H), 2.21 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-71-1, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 97004-04-1, 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 97004-04-1, name is (6-Chloropyridin-3-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a Radley reaction carousel tube, add 1 equivalent 1, 1.1 equivalents of the amine, a stir bar, and 5 mL 95% ethanol. Reflux while stirring for 24 hours. After cooling to room temperature the resulting precipitate was collected by vacuum filtration, washing with 10 mL deionized water and 5 mL chloroform.

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 97004-04-1, (6-Chloropyridin-3-yl)methanamine.

Reference:
Article; Watkins, Sydney M.; Ghose, Debarati; Blain, Joy M.; Grote, Dakota L.; Luan, Chi-Hao; Clare, Michael; Meganathan; Horn, James R.; Hagen, Timothy J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 685115-77-9, 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 685115-77-9 as follows.

To a mixture of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (24 mg, 0.088 mmol), 3,4-diimethoxyphenyllboronic acid (19 mg, 0.11 mmol), and tetrakis (triphenylphosphine)palladium(O) (5 mg, 5 mol%) in acetonitrile (1 ml.) was added a 0.5 M aqueous solution of sodium carbonate (0.25 ml_, 0.12 mmol). The mixture was heated at 150 0C in a microwave reactor for 45 min, then cooled to r.t. and purified on an SCX-2 cartridge (MeOH followed by 0.5 M NH3 in MeOH). The crude product was purified by preparative tic on silica gel (CH2CI2, MeOH, 10:1 ) to give impure title compound (7 mg). Further purification by preparative hplc (H2O, MeCN, 90:10-10:90, 30 min) furnished the title compound as a white solid, LC-MS (ESI, 3.5 min) R, 1.60 min, m/z 376 (100%, [M+H]+); mlz (ESI) C19H23CIN3O3 requires 376.1428 found [M+H]+ 376.1421.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,685115-77-9, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem