Month: April 2022

Electric Literature of 1187322-51-5, 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. 1187322-51-5, name is 6-Amino-5-iodonicotinonitrile, molecular formula is C6H4IN3, 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.

1.2 g 5-[4-(6-trimethylsilanyl-hex-5-ynyl)-piperazin-1-yl]-benzofuran-2- carboxylic acid amide, 500 mg beta-amino-delta-iodo-nicotinonitrile, 0.1 g lithium chloride, 0.8 g sodium carbonate and 0.1 g 1,1′-bis(diphenyl- phosphino)ferrocenedichloropalladium- (II) dichloromethane adduct were dissolved in 50 ml DMF and heated for 12 h. The black suspension was poured on 50 ml water and extracted with ethyl acetate. After the usual extraction and purification procedure 20 mg of fawn amorphous solid 5-{4-[4-(5-cyano-1 H-pyrrolo[2,3-b]pyridine-3-yl)-butyl]- piperazin-1-yl}-benzofuran-2-carboxylic acid amide were obtained. 1H-NMR (500MHz, dbeta-DMSO) delta 12.18 (br s, 1H)1 8.49 (d, 1 H, J = 1.8 Hz), 8.33 (d, 1 H, J = 1.8 Hz), 7.99 (br. s, 1 H), 7.57 (br. s, 1 H), 7.47 (d, 1H1 J = 9.9 Hz), 7.40 (s, 1 H), 7.17 (m, 2H), 6.35 (s, 1 H), 3.33 (m, 4H), 3.11 (m, 4H)1 2.81 (m, 2H), 2.38 (m, 2H), 1.76 (m, 2H), 1.54 (m, 2H). P08033 HN.doc27HPLC-MS: Chromolite SpeedROD RP-18e 50-4, 6 mm solvent A: water + 0.1 % TFA solvent B: acetonitrile + 0.1% TFA 5 flow: 2.4 mL/min gradient: 0,0 min 4% B2.6 min 100% B Rt: 1.909 min[M+H]+: 398

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 1187322-51-5, 6-Amino-5-iodonicotinonitrile.

Reference:
Patent; MERCK PATENT GMBH,; WO2009/112139; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137520-99-1 ,Some common heterocyclic compound, 137520-99-1, molecular formula is C9H9Cl2NO2, 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 mixture of 2,6-dichloro-3-methylisonicotinic acid ethyl ester (10.0 g, 42.7 mmol), Example 7E and acetic acid (2.69 g, 44.9 mmol) in carbon tetrachloride (147 ml.) are added lambda/-bromosuccinimide (8.36 g, 47.0 mmol) and then benzoyl peroxide (1.03 g, 4.27 mmol). The mixture is stirred in oil bath at 60 0C under heat lamp for 5 h. The mixture is then cooled to room temperature. About half of the solvent is removed by rotary evaporation. The white succinimide solid is removed by filtration. The overweight filtrate (17 g for a theoretical 13.4 g, 42.7 mmol) is concentrated under reduced pressure and used as a crude immediately for the next step. MS(ESI) m/z 313.99. 1H NMR (400 MHz1CDCI3) delta ppm 7.72 (s, 1 H), 4.99 (s, 2 H), 4.48 (q, J=7.16 Hz, 2 H), 1.46 (t, J=7.07 Hz, 3 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. 137520-99-1, Ethyl 2,6-dichloro-3-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

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

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.52538-09-7, name is 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine, molecular formula is C8H9N3, molecular weight is 147.18, as common compound, the synthetic route is as follows.Product Details of 52538-09-7

To a solution of 2,3-dimethyl-3H-imidazo[4,5-c]pyridine (0.31 g, 2.14 mmol) in 3.5 ml 1,4-dioxine, selenium dioxide (356 mg, 3.21 mmol) was added and the mixture was heated by microwave under 1500C for 30 minutes. The mixture was filtered and the solvent was removed in vacuo. The residue purified using silica gel chromatography (0% to 10% MeOH/CH2CI2) to yield 3-methy|-3H-imidazo[4,5-c]pyridine-2-carbaldehyde (0.15 g); GC-MS 161.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52538-09-7, 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12622; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89809-63-2, 5-Methoxypicolinonitrile, 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, 89809-63-2, blongs to pyridine-derivatives compound. Safety of 5-Methoxypicolinonitrile

General procedure: To a solution of diisopropylamine (170 muL, 1.2 eq.) in dry THF (2 mL) in a flame dried round bottom flask under argon at 0 C was added n-butyllithium (690 muL, 1.6 M in hexanes, 1.1 eq.), and the reaction mixture was stirred at this temperature for 15 minutes. It was then cooled to -78 C and a solution of ketone (1) (1 mmol) in THF (2 mL) slowly added. Stirring at -78 C was continued for a further 30 minutes and methyl chlorosulfate (100 muL, 1.1 eq.) was then added. After stirring at -78 C for 30 minutes, the reaction was quenched with an aqueous saturated ammonium chloride solution (5 mL). The mixture was then extracted with dichloromethane (3 x 5 mL), the combined organic phases were dried with anhydrous magnesium sulfate and the solvent evaporated under vacuum affording the desired alpha-chloroketone 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89809-63-2, its application will become more common.

Reference:
Article; Silva, Saul; Maycock, Christopher D.; Tetrahedron Letters; vol. 59; 13; (2018); p. 1233 – 1238;,
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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2Cl3N

In a 1000 ml stainless steel autoclave, 50 g of 2,3,6-trichloropyridine was added.300g of methanol, 35g of triethylamine, and then added 0.05g of 10% palladium carbon.First replace the air in the kettle three times with nitrogen, and then replace it three times with hydrogen.Pressurize to 4.0Mpa and control the temperature at 45~50C.The reaction speed was set to 300 rpm/min, and hydrogen was continuously added during the reaction.The reaction pressure was maintained at 3.0 to 4.0 MPa, and the reaction was stopped after 4 hours of reaction.Cooling, sampling for liquid phase quantitative detection and analysis,The conversion rate of raw material 2,3,6-trichloropyridine is 96.5%.The selectivity to 2,3-dichloropyridine was 86.7%. After filtering the reaction solution,After rectifying and removing the reaction solvent, after adding a moisture layer,The organic phase was subjected to rectification to obtain 33.1 g of a white 2,3-dichloropyridine product.The product purity is 99.5%.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Patent; Chongqing Zhong Bang Technology Co., Ltd.; Wang Ping; Lai Ming; Mu Xinbin; Jiang Cheng; Li Xueping; (5 pag.)CN109280026; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75073-11-9, 5-Iodo-6-methylpyridin-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, 75073-11-9, blongs to pyridine-derivatives compound. Quality Control of 5-Iodo-6-methylpyridin-2-amine

To a suspension of 2 g of 5-iodo-6-methylpyridine-2-amine in 15 mL of dimethoxyethane are added 1.3 mL of ethyl bromopyruvate. The reaction mixture is stirred at 20 C. for 16 hours and then concentrated to dryness, taken up in 15 mL of ethanol, refluxed for 2.5 hours and finally concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 2.77 g of ethyl 6-iodo-5-methyl(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylate in the form of a beige-coloured solid.1H NMR spectrum (DMSO-d6, delta in ppm): 1.33 (t, J=7.1 Hz, 3H), 2.84 (s, 3H), 4.33 (q, J=7.1 Hz, 2H), 7.34 (d, J=9.3 Hz, 1H), 7.66 (d, J=9.3 Hz, 1H), 8.48 (s, 1H).Mass spectrum (LC-MS-DAD-ELSD): m/z 331 [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,75073-11-9, its application will become more common.

Reference:
Patent; sanofi-aventis; US2010/317675; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2369-19-9, 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 2369-19-9, name is 2-Fluoro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (252 mL, 1.80 mmol) in anhydrous tetrahydrofuran (5 mL) was added under argon at 20 C, a 2.5 M solution of n-butyllithium in hexanes (719 mL, 1.80 mmol). After stirring at 20 C for 30 min, the reaction was cooled to 78 C, then a solution of 2-fluoro-5-methylpyridine (14) [27] (200 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added over 10 min. The reaction was stirred at 78 C for 3.5 h, then a solution of iodine (457 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added. The mixture was stirred at 78 C for additional 1 h, before quenching with a solution of water (2 mL) and tetrahydrofuran (10 mL). After warming to 0 C, the mixture was diluted with water (50 mL) and sodium bisulfite was added until a colorless solution was obtained. After extraction with dichloromethane (3 x 30 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/cyclohexane, 5/5, v/v) to give 2-fluoro-3-iodo-5-methylpyridine (15) (275 mg, 1.16 mmol) as a colorless solid. Yield 65%; Rf (SiO2, dichloromethane/cyclohexane, 5/5, v/v) 0.21; mp 40-45 C; IR (KBr) nu 1049, 1379, 1446, 2930 cm-1; 1H NMR (200 MHz, CDCl3) delta 2.28 (s, 3H, CH3), 7.95 (m, 2H, H-4, H-6); 13C NMR (50 MHz, CDCl3) delta 17.0 (CH3), 75.4 (d, 2JC-F = 44 Hz, C-3), 132.7 (d, 4JC-F = 5 Hz, C-5), 146.8 (d, 3JC-F = 13 Hz, C-6), 150.4 (C-4), 160.4 (d, 1JC-F = 232 Hz, C-2); 19F NMR (470 Mz, CDCl3) 61.7; ESI-MS m/z 237.89 [M+H]+.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100367-55-3 , The common heterocyclic compound, 100367-55-3, name is 5-Nitropicolinonitrile, molecular formula is C6H3N3O2, 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 X1 (149 mg, 1.0 mmol), NaOCH3 5.4 mg (0.1 mmol) and 10.0 mL CH3OH was placed in the 50 mL flask and reacted at 40 C for 1 h. Then methylaminoacetaldehyde dimethyl acetal 105.0 mg (1.0 mmol) and CH3COOH 0.5 mL were added into the reaction mixture refluxed for 30 min. After that CH3OH 5.0 mL and CH3COOH 1.0 mL were added to and refluxed for another 4.5 h. Then pH of the resulting mixture was adjusted to 10. The resulting precipitates were collected by filtration and washed with water (30 mL x 2) to give the crude material. The resulting crude material was purified by recrystallization with methanol to afford compound X2 133.0 mg (70.0 %). mp: 202-203 C. 1H NMR (300 MHz,DMSO-d6): delta 7.23 (s, 1H, CH-imidazole), 7.40 (s, 1H, CH-imidazole), 8.23 (d, 1H, 3-H, J = 8.8 Hz), 8.64 (dd, 1H, 4-H, J = 2.6 Hz and J = 8.8 Hz), 9.36 (d, 1H, 6-H, J = 2.6 Hz), 13.2 (s, 1H, NH-imidazole). IR (KBr): 3153, 3109, 1600, 1579, 1471, 1383, 1118, 858 cm-1.

The synthetic route of 100367-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiao, Yu; Xin, Bo-Tao; Zhang, Yanmin; Wu, Jianbing; Lu, Xiaolin; Zheng, Ying; Tang, Weifang; Zhou, Xiang; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 170 – 183;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, the common compound, a new synthetic route is introduced below. Safety of 5-(Trifluoromethyl)pyridin-3-amine

To a stirred solution of Example 30A (100 mg, 0.62 mmol) and triethylamine (75 mg, 0.74 mmol) at0 C in dichloromethane (5 ml) is added ethyl malonyl chloride (108 mg, 0.65 mmol) dropwise over 15 minutes. The solution is allowed to warm to room temperature, and stirring is continued overnight (18 h). The crude reaction solution is concentrated in vacuo and the residue is purified by preparativeRP-HPLC (acetonitrile/water 1: 9 to 9: 1 gradient) to afford a colourless oil. Yield: 144.4 mg(85% of th.)HPLC (method 5): Rt = 3.80 min. , max 196 nm, 244 nm MS (ESIpos):m/z = 277[M+H] +H-NMR (300MHz, CDC13) :8 = 9.74 (s, 1H); 8.81 (s, 1H); 8.64 (s, 1H) ; 8.47 (s,1H) ; 4.30 (q, 2H); 3.53 (s, 2H);1. 35 (t, 3H) ppm.

The synthetic route of 112110-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20410; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156072-84-3, 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 156072-84-3 as follows.

(5-chloro-3-methylpyridin-2-yl)methanamine5-chloro-3-methylpyridine-2-carbonitrile (0.50 g; 3.28 mmol; 1.00 eq.) was dissolved in 7M ammonia/methanol (16 ml) and ethanol (16 ml) with Raney Ni which had been rinsed with ethanol 3×. The reaction was charged with H2 and stirred vigorously. After 21 h, the reaction was filtered through Celite, evaporated to a reddish-blue residue of (5-chloro-3-methylpyridin-2-yl)methanamine which was carried on without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem