Category: pyridine-derivatives

Related Products of 62135-58-4, 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. 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

Under argon atmosphere, ethyl [l,2,4]triazolo[l,5-a]pyridine-2-carboxylate (1 g, 5.23 mmol) was combined with THF (10 mL) at RT to give a brown suspension. Sodium borohydride (1.19 g, 31.4 mmol) was added in four portions. The mixture was heated to 65 C for 15 min. After cooling down to RT, ethanol (10 mL) was added dropwise over a period of 15 min. The mixture was stirred at 65 C for 4 h. The mixture was cooled down to 0-5 C and NH4C1 (saturated aqueous solution, 20 mL) was added dropwise over a period of 10 min (foam.). Water (20 mL) was added and the yellow suspension was poured into dichloromethane (100 mL) and extracted with dichloromethane (4 x 75 mL). The combined organic layer was dried over MgS04 and concentrated in vacuo to give the product as light yellow solid (720 mg, 4.76 mmol, 91 %) which was used without further purification for the next step.MS: M = 150.1 (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,62135-58-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BACHMANN, Stephan; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RUDOLPH, Markus; WO2013/34506; (2013); 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Potassium bis(trimethylsilyl)amide (25 mL, 12.5 mmol, 0.5M in toluene) was added to a solution of 2-amino-5-bromo-nicotinonitrile (496 mg, 2.5 mmol) in THF (10 mL) at -78 0C which was followed by a dropwise addition of acetyl chloride (533 muL, 7.5 mmol). The reaction was stirred at ambient temperature for 4 h then quenched with ammonium chloride (10 mL, sat). The resulting mixture was extracted with methylene chloride; the organic layer was washed with water and dried over MgSO_j. The volatiles were removed under vacuum to give the title compound (420 mg, 70%). 1H NMR (300 MHz, DMSO-4 delta): 10.92 (s, IH), 8.82 (d, J = 2.3Hz, IH), 8.66 (d, J= 2.3Hz, IH), 2.12 (s, 3H). MS (ESI) m/e: 240 and 242 (M+H)+.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
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Pyridine | C5H5N – PubChem

Related Products of 185315-53-1 , The common heterocyclic compound, 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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.

Synthesis of 4.5-dichloro-2-((3-chloropyridin-2-vnmethvnpyridazin-3(2HV one (G3-2 32 G3-2 To a solution of compound 4 (200 mg, 1.21 mmol), compound 32 (235 mg, 1.45 mmol) and K2CQ3 (335 mg, 2.42 mmol) in DMF (3 mL) was added KI (20 mg, 0.12 mmol). The solution was stirred at 90 C for 2h. The mixture was cooled to room temperature and quenched with water, extracted with EtOAc for 3 times, combined the organic layer, washed with brine, dried over Na2S(X filtered, concentrated under reduced pressure, purified by HPLC to give G3-2 (126 mg, 42%) as a yellow solid. NMR (DMSO-ifc, 300 MHz): delta 5.53 (s, 2H), 7.38-7.42 (m, 1H), 7.99 (d, J = 8.1 Hz, 1H), 8.27 (s, 1H), 8.41 (d, J = 4.5 Hz, 1H); LCMS [mobile phase: 20-95% Acetonitrile +0.02% NHtOAc] purity is >95%, Rt = 3.365 min; MS Calcd.: 290; MS Found: 291 (M+l)+.

The synthetic route of 185315-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; BECKWITH, Jonathan Roger; DUTTON, Rachel; ESER, Markus; LANDETA, Cristina; BLAZYK, Jessica L.; MEEHAN, Brian M.; HATAHET, Feras; BOYD, Dana; WO2015/143164; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1079179-12-6 ,Some common heterocyclic compound, 1079179-12-6, molecular formula is C5H2ClFN2O2, 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 2-chloro-3-fluoro-5-nitropyridine (3.0 g, 15.3 mmol) in DMF (30 mL) was added thiomorpholine (1.6 g, 15.3 mmol) and DIEA (5.3 mL, 30.6 mmol). The mixture was stirred at 60C for 16 hours. The reaction was cooled to roomtemperature, and then then was diluted with water (50 mL). The precipitated solid was collected by filtration, and dried to give 4-(3-fluoro-5-nitropyridin-2-yl)thiomorpholine asa solid. ?HNMRoe 8.87 (s, 1H), 7.98 (dd, J= 2.0, 13.6Hz, 1H), 4.15-4.12 (m, 4H), 2.76-2.74 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1079179-12-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YANG, Lihu; OLSEN, David B.; YOUNG, Katherine; SU, Jing; MANDAL, Mihir B.; SUZUKI, Takao; YOU, Lanying; (85 pag.)WO2017/66964; (2017); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

At -78 C., 19.6 ml of 1.9 mol/L solution of hexamethyldisilazane sodium in THF was added dropwise to 100 ml of THF solution containing 2.00 g of 2-(2-chloropyridin-3-yl)acetic acid, and the mixture was stirred for 10 minutes. Next, 1.50 ml of methyl p-fluorobenzoate was added dropwise. The mixture was then brought from -78 C. to room temperature and was stirred for 1 hour. Saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred. Thereafter, ethyl acetate was added, and the resultant liquid mixture was separated. The obtained organic layer was washed with saturated brine and was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography. The title compound was obtained as a colorless amorphous compound weighing 1.45 g. 1H-NMR(CDCl3)delta:8.36(1H,dd,J=4.6,1.9 Hz),8.11-8.07(2H,m),7.62(1H,dd,J=7.4,1.9 Hz),7.27-7.24(1H,m),7.21-7.17(2H,m),4.42(2H,s).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; FUKUMOTO, Takeshi; NAITO, Ryohei; IKISHIMA, Hideaki; KOUNO, Toshiyuki; NISHIDA, Akihiro; YANAGI, Masanori; KITAJIMA, Kazuki; YUTANI, Satoshi; SHIRAKAWA, Tomomi; OHARA, Toshiaki; (170 pag.)US2019/380340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-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, HPLC of Formula: C8H6N2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C8H6N2O2

General procedure: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Example 29 6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C. in phosphorus tribromide (150 mL) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 mL), and the mixture was heated at 145 C. for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 mL) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3*250 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J=11.0 Hz, 1H), 7.80 (dd, J=3.1, 11.0 Hz, 1H), 8.67 (d, J=3.1 Hz, 1H); MS (M+H)+ m/z=183.0, 185.0.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; Xue, Chu-Biao; Metcalf, Brian W.; Han, Amy Qi; Robinson, Darius J.; Zheng, Changsheng; Wang, Anlai; Zhang, Yingxin; US2005/192302; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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, 52378-63-9, blongs to pyridine-derivatives compound. HPLC of Formula: C6H8N2O

(i) A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-chloro-2-hydroxymethylpyridine (3.7 g), m.p. 42-44 (from n-pentane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52378-63-9, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4025527; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884495-38-9 ,Some common heterocyclic compound, 884495-38-9, molecular formula is C7H6ClNO, 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.

General procedure: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 % MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70%) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-38-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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: 153747-97-8

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (5OmL), 4N HCI solution in dioxane (100 mL, IOV) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residuewas washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 6 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, IH), 7.82 (dd, J = 9.2, 2.4 Hz, IH), 6.99 (d, J = 9.2 Hz, IH), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 mm, 99.3 % (Max).

With the rapid development of chemical substances, we look forward to future research findings about 153747-97-8.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem