Category: pyridine-derivatives

Application of 62150-45-2 , The common heterocyclic compound, 62150-45-2, name is 4-Bromopyridine-2-carbonitrile, molecular formula is C6H3BrN2, 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.

Step 1. 4-Bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine 4-Bromopyridine-2-carbonitrile (1.0 g, 5.5 mmol, Synthonix) in MeOH (10 mL) was treated with sodium methoxide (25 wt percent in MeOH, 0.095 mL, 0.47 mmol) and the reaction was stirred for 1 hour. Ammonium chloride (0.37 g, 6.9 mmol) was added and the reaction was stirred for 4 days. Solvent was then removed in vacuo. Water (4 mL) and EtOAc (6 mL) were added, the mixture was saturated with solid NaCl, and the mixture was stirred overnight. The solid product was isolated by filtration and dried at 40° C. under vacuum overnight. The product was used below without further purification. To 4-bromopyridine-2-carboximidamide (0.50 g, 2.5 mmol) in DMF (5 mL) was added K2CO3 (0.52 g, 3.7 mmol) and 3-bromo-2-butanone (0.24 mL, 3.2 mmol). The reaction was stirred for 4 days. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with two further portions of EtOAc. The combined organic extracts were washed sequentially with water and saturated NaCl solution. The organic solution was dried over Na2SO4, filtered, and concentrated. The crude product was triturated with methyl tert-butyl ether (MTBE, 2 mL) and the solid product was isolated by filtration and dried under vacuum at 40° C. for 3 hours. Yield: 372 mg, 59percent. LCMS (M+H)+: 252.0/254.0.

The synthetic route of 62150-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Sparks, Richard B.; Shepard, Stacey; Combs, Andrew P.; Buesking, Andrew W.; Shao, Lixin; Wang, Haisheng; Falahatpisheh, Nikoo; (158 pag.)US2017/190689; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1188477-11-3, 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. 1188477-11-3, name is tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl ((5-bromopyridin-2-yl)methyl)carbamate (2.2 g, 7.7 mmol) in 1,4-dioxone (4 mL) was added a solution of HCl in 1,4-dioxane (20 mL, 60 mmol, 3 M HCl in 1,4-dioxane). The mixture was stirred at 28C for 2 hr then concentrated to dryness to give the crude product (2.2 g crude) as yellow solid which was directly used in the next step without further purification. LC-MS: m/z 186,188 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1188477-11-3, tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1628-89-3, Adding some certain compound to certain chemical reactions, such as: 1628-89-3, name is 2-Methoxypyridine,molecular formula is C6H7NO, 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 1628-89-3.

A: 2 mol of 6-methoxypyridine and 700 ml of a 22percent potassium chloride solution were added to the reaction vessel.1.2L mass fraction of 26percent heptane solution, control solution temperature to 15 ° C,Adding an aqueous solution, 6 mol of aluminum isopropoxide, controlling the stirring speed of 370 rpm, and continuing the reaction for 120 min; B: Then, 6 mol of antimony trichloride powder was added, the temperature was controlled at 26 ° C, the reaction was continued for 3 h, then the temperature was lowered to 8 ° C, allowed to stand for 50 min, and the solution was layered.The oil layer was separated and washed 5 times with a 15percent sodium sulfate solution.The solution was washed 8 times with a mass fraction of 77percent in xylene and recrystallized from a cyclohexene solution having a mass fraction of 86percent.The dehydrating agent was dehydrated with anhydrous sodium sulfate to obtain 216.038 g of the obtained N-methylpyridin-2-one, and the yield was 99.1percent.

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Kadifu Technology Co., Ltd.; Liao Runai; (4 pag.)CN108239022; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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. 1620-77-5, name is 5-Methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Synthesis Example 1 Ethyl 5-methylpyridine-2-carboxylate STR24 200 ml of ethanol and 100 ml (1.88 mol) of concentrated sulfuric acid were added to 55.5 g of 5-methylpyridine-2-carbonitrile to form a homogeneous solution, followed by heating under reflux for 2 days. The reaction liquid was gradually poured into a saturated aqueous solution of sodium hydrogencarbonate under cooling with ice to neutralize the sulfuric acid, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 78.1 g of a brown oil of the title compound as the crude product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1620-77-5, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US5789403; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72716-87-1 , The common heterocyclic compound, 72716-87-1, name is 2-Methoxyisonicotinaldehyde, molecular formula is C7H7NO2, 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.

Nitrosonitric acid (1 mL) was added dropwise to a solution of 2-methoxypyridine-4-formaldehyde (137 mg, 1.0 mmol) in trifluoroacetic anhydride (2 mL) at room temperature. The reaction mixture was stirred at 25 C for 3 days, and then was poured into ice-water mixture, followed by the addition of saturated sodium carbonate solution to adjust the pH value to exceed 10. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried and concentrated. The resulting residue was dissolved in toluene (5 mL), and toluene-p-sulfonic acid (5 mg) and glycol (105 mg, 1.7 mmol) were added. The reaction mixture was heated to reflux and reacted overnight. After cooled, the mixture was washed with saturated sodium carbonate solution and brine, dried, and concentrated under vacuum. The resulting residue was dissolved in methanol (10 mL), added Pd/C catalyst (20 mg), and introduced into hydrogen gas. The reaction system was stirred for 2 h under 1 atm hydrogen, then filtered to remove the catalyst, and concentrated under vacuum to remove the solvent. The residue was purified by column chromatography to obtain the title compound (15 mg, 8 %). 1H NMR (DMSO-d6): delta 9.31 (1H, s), 8.56 (1H, s), 7.42 (1H, s), 7.34 (1H, s), 6.55 (1H, s), 5.43 (2H, s), 5.30 (2H, s), 4.02 (3H, s), 2.04-1.91 (2H, m), 0.90-0.85 (3H, m).

The synthetic route of 72716-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 35905-85-2, 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. 35905-85-2, name is 2-Bromonicotinic acid. A new synthetic method of this compound is introduced below.

Step 2: Methyl 2-bromonicotinate (G2); A solution of of CH2N2 (4 eq.) in Et2O (1 M) was added dropwise to a solution of 2- bromonicotinic acid in THF (0.5 M) at RT. The reaction mixture was stirred at room temperature overnight, then quenched by dropwise addition of AcOH (4 eq.). The organic phase was washed with water and brine and dried (MgSO4). Evaporation of the solvent yielded (75%) the title compound which was used in the next step without further purification. 1H NMR (300MHz, CDCl3, 300K) delta 8.47 (IH, dd, J= 4.8 Hz, 2.1 Hz), 8.07 (IH, dd, J= 7.8 Hz, 2.1 Hz), 7.35 (IH, dd, J= 7.5 Hz, 4.5 Hz), 3.93 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,35905-85-2, 2-Bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/112832; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57266-69-0, 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. 57266-69-0, name is 3-Chloropicolinic acid. A new synthetic method of this compound is introduced below.

To a solution of 3-chloropicolinic acid (20.006 g, 126.98 mmol) in toluene (200 mL) was added thionyl chloride (23.2 mL, 37.8 g, 317 mmol, 2.5 equiv.) and a catalytic amount of DMF (10 drops) and the mixture was heated at reflux for 1 h. After cessation of the gas evolution, the mixture was cooled and all volatiles were removed in vacuum to obtain to obtain the title compound (24.38 g, quant.) as a crude product, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57266-69-0, 3-Chloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; DESHMUKH, Prashant; KOeRBER, Karsten; KAISER, Florian; KORDES, Markus; DICKHAUT, Joachim; NARINE, Arun; BANDUR, Nina Gertrud; VEITCH, Gemma; CULBERTSON, Deborah L.; NEESE, Paul; GUNJIMA, Koshi; WO2013/24006; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-14-2, 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. 83004-14-2, name is 2-Bromo-4-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 59 A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (950 mg, 3 mmol), (prepared as described for the starting material in Example 24), 2-bromo-4-bromomethylpyridine (765 mg, 3 mmol) and potassium carbonate (2.38 g 17 mmol) in DMF (10 ml) was heated at 80 C. for 2 hours. The mixture was allowed to cool, poured into water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent removed by evaporation and azeotroped with toluene. The residue was triturated with ethyl acetate/hexane and the solid product collected by filtration, washed with ethyl acetate/hexane and dried to give 7-((2-bromo-4-pyridyl)methoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (647 mg, 44%). m.p. 210-212 C. 1 H NMR Spectrum: (DMSOd6) 3.98(s, 3H); 5.40(s, 2H); 7.25(s, 1H); 7.30(d, 1H); 7.50(s, 1H); 7.50(d, 1H); 7.55(m, 2H); 7.74(s, 1H); 7.86(s, 1H); 8.35(br s, 1H); 8.42(d, 1H); 9.56(s, 1H) MS – ESI: 489 [MH]+ Elemental analysis: Found C 52.0 H 3.2 N 11.2 C21 H15 N4 O2 BrClF Requires C 51.5 H 3.1 N 11.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83004-14-2, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
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. 34160-40-2, name is 6-Bromo-2-pyridinecarboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-2-pyridinecarboxaldehyde

Step 1: Synthesis of 2-bromo-6-(difluoromethyl)pyridine (0396) 3.81 g (23.6 mmol) of (diethylamino)sulfur trifluoride were added with ice cooling to a mixed solution of 2.00 g (10.8 mmol) of 6-bromopicolinaldehyde and 40 ml methylene chloride. After completion of the addition, said reaction mixture liquid was stirred for 2 hours with ice cooling. After completion of the stirring, the reaction was stopped by addition of 30 ml of saturated aqueous sodium hydrogen carbonate solution, and said reaction liquid was extracted with methylene chloride (2×30 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=10:0 to 8:2), and 1.87 g of the desired compound were obtained as a white solid. (0397) 1H-NMR (CDCl3, Me4Si, 300 MHz): delta 7.73-7.58 (m, 3H), 6.58 (t, 1H, J=56 Hz).

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, 34160-40-2, 6-Bromo-2-pyridinecarboxaldehyde.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; NAKAYA, Yoshihiko; MASUZAWA, Yoshihide; FURUHASHI, Takamasa; MIYAKADO, Yuuki; HOTTA, Hiroyasu; INABA, Masamitsu; (76 pag.)US2016/221998; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 754230-78-9 ,Some common heterocyclic compound, 754230-78-9, molecular formula is C12H11BrN2O, 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 85A Ethyl 8-(benzyloxy)-6-bromo-2-methylimidazo[1,2-a]pyridine-3-carboxylate Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine Example 84A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g 3 A molecular sieve were suspended in 6 l of ethanol and boiled at reflux for 72 h. The reaction mixture was filtered off through kieselguhr and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate 9:1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound. LC-MS (Method 17): Rt=1.31 min MS (ESpos): m/z=389 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,754230-78-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem