Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 2524-52-9, Ethyl 2-picolinate, 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, COA of Formula: C8H9NO2, blongs to pyridine-derivatives compound. COA of Formula: C8H9NO2

To a solution of 73-3 (5.0 g, 1 equiv.) in EtOH (30 mL) was added NH2NH2H2O (2.5 g, 1.5 equiv.). Then the mixture was heated to reflux and stirred for 16 h. The reaction was completed. The reaction mixture was cooled to room temperature and concentrated to get 4.6 g of crude 73-4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2524-52-9, Ethyl 2-picolinate, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY; JACOBS, Robert Toms; LIU, Yang; SCIOTTI, Richard J.; (0 pag.)WO2018/160845; (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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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: 13466-38-1

A mixture of 5-bromopyridin-2-ol (I-99, Aldrich, Wis.; 53 g, 0.30 mol) in concentrated.H2SO4 (250 mL) was stirred with ice bath cooling and concentrated HNO3 (105 mL) was added slowly to the mixture. The reaction mixture was stirred for 4 hours at room temperature and then poured onto ice and stirred for additional 30 minutes. A yellow precipitate was filtered off used in the following step without further purification (45 g, 68%). MS (ESI): m/z 220 (M+1)+.

With the rapid development of chemical substances, we look forward to future research findings about 13466-38-1.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); 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. 176433-49-1, name is 2,5-Dichloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 176433-49-1

(a) 2-Pyrid-4-ylbenzaldehyde: In a similar manner to that of Example 21(a), starting with 2.50 g (16.7 mmol) of 2-formalbenzeneboronic acid and 2.16 g (11.1 mmol) of 4-bromopyridine hydrochloride, 1.98 g (97%) of the expected compound are obtained in the form of a white powder with a melting point of 59 C. 1 H NMR (CDCl3) delta 7.33 (d, 2H, J=6.0 Hz), 7.43 (dd, 1H, J=8.4/0.9 Hz), 7.59 (t, 1H, J=7.4 Hz), 7.70 (dt, 1H, J=7.5/1.4 Hz), 8.07 (dd, 1H, J=7.6/1.1 Hz), 8.73 (d, 2H, J=6.0 Hz), 9.99 (s, 1H).

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, 176433-49-1, 2,5-Dichloronicotinaldehyde.

Reference:
Patent; Centre International de Recherches Dermatologiques; US6150413; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39891-13-9, 2-(6-Chloropyridin-3-yl)acetic 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, 39891-13-9, blongs to pyridine-derivatives compound. Quality Control of 2-(6-Chloropyridin-3-yl)acetic acid

To a stirred solution of 329 2-(6-chloropyridin-3-yl)acetic acid (10 g, 58.3 mmol) in 6 DCM (100 mL) and 139 MeOH (50 mL) was added 330 ((trimethylsilyl)methyl)diazene (8.3 mL, 175 mmol) at 0 C. The reaction was stirred at RT for 16 h and then the solvent was concentrated under reduced pressure. The residue was dilute with water (100 mL), extracted with EtOAc (100 mL×3), and the organic layers were collected, washed with brine (50 mL), dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography to afford the 331 title compound as an oil. MS (ESI) m/z: 185.8 [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,39891-13-9, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]pyridine, 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 1206979-33-0, blongs to pyridine-derivatives compound. Product Details of 1206979-33-0

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate (530 mg, 1.33 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (203 mg, 1.33mmol) in 1,4-dioxane (30 mL) was added Cul (101 mg, 0.53 mmol), N1,N2-dimethylethane-1,2-diamine (94 mg, 1.06 mmol), and K2CO3 (734 mg, 5.32 mmol). The mixture was heated at 100C, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using petroleumether:EtOAc (3:1~1:1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate as yellow solid. (446 mg, 71%). MS (ESI) m/z: 473 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); 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. 147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 147149-98-2

POCl3 (98.85 mg, 0.65 mmol) was added to a mixture of 1-(2-methylimidazo[1,2-a]pyridin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (100 mg, 0.32 mmol), 2-(trifluoromethyl)pyridin-4-amine (52.26 mg, 0.32 mmol), pyridine (127.49 mg, 1.61 mmol) in CH2Cl2 (3 mL) at rt. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with 20 mL sat. K2CO3 aq, and extracted with CH2Cl2 (20 mL*3). The organic layer was separated and concentrated under reduced pressure. It was purified by preparative high-performance liquid chromatography (35% to 65% (v/v) CH3CN and H2O with 0.05% ammonia hydroxide). The pure fractions were collected and the organic solvent was concentrated under reduced pressure. The aqueous layer was lyophilized to dryness to give the desired product as a white solid. (80 mg, purity: 99.5%, yield: 54.3%). LCMS (ESI) m/z M+1: 454.9. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.32 (s, 3H), 7.08 (s, 1H), 7.32 (d, J=7.06 Hz, 1H), 7.41 (dd, J=9.04, 7.28 Hz, 1H), 7.75 (d, J=9.04 Hz, 1H), 7.94 (dd, J=5.73, 1.76 Hz, 1H), 8.21 (d, J=1.76 Hz, 1H), 8.65 (s, 1H), 8.69 (d, J=5.29 Hz, 1H), 11.29 (s, 1H).

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, 147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 133427-08-4, 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.133427-08-4, name is Imidazo[1,2-a]pyridine-8-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.

Step E: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).To a solution of imidazo[l,2-alpha]pyridine-8-carboxylic acid (36.6 mg, 226 mumol), l-(2,4- difluorophenethyl)piperazine hydrochloride (45.0 mg, 150 mumol) and triethylamine (210 mul, 1504 mumol) in DMF (0.75 mL) was added 1-propylphosphonic acid anhydride solution (50% in ethyl acetate, 183 muL, 0.301 mmol). The mixture was stirred for 2 h, quenched with water and purified by preparative HPLC/MS. The resultant lyophilate was dissolved in DCM, treated with MP-carbonate resin (-200 mg). The mixture was stirred for 30 min and filtered to remove the resin. The solvent was removed under reduced pressure to afford the title compound as a white solid (33.0 mg).

Statistics shows that 133427-08-4 is playing an increasingly important role. we look forward to future research findings about Imidazo[1,2-a]pyridine-8-carboxylic acid.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H8N2O

To a stirring suspension of (6-aminopyridin-3-yl)methanol (1 .24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0mmol) in EtOH (10 mL) at room temperature was added cone sulfuric acid (1 0.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6- (hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1 H NMR (400MHz, c/6-DMSO) delta 9.16 (d, J = 6.8 Hz, 1 H), 8.26 (s, 1 H), 7.67 (s, 1 H), 7.19 (dd, J = 1 .6, 6.8 Hz, 1 H), 5.57 (t, J = 6.4 Hz, 1 H), 4.63 (d, J = 6.0, 2H), 4.36 (q, J = 7.2 Hz, 2H), 1 .35 (t, J = 6.8 Hz, 3H). MS m/z 221 .1 (M+1 ) +.

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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; IRM LLC; LOREN, Jon; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; RUCKER, Paul Vincent; WO2013/33203; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 128372-89-4, 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. 128372-89-4, name is tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H15NO3, 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: A dried Schlenk flask was charged with arylboronic acid (3, 0.4 mmol), [Rh(L1)(OH)]2 (L1=(S,S)-Ph-thpe, 3.8 mg, 0.005 mmol), KHF2 (3.2 mg, 0.04 mmol), and 1 mL of anhydrous toluene under argon. The resulting mixture was stirred at room temperature for 30 min. 1-N-Boc-2-oxo-5,6-dihydropyridine (2c, 39.4 mg, 0.2 mmol) in toluene (1 mL) was added. Seven minutes later, 0.1 mL of isopropanol was added. After being stirred at room temperature for 2 h, the reaction was quenched with saturated aq NH4Cl, extracted with ethyl acetate (20 mL×3), and the combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel (300-400 mesh) column chromatography to afford 4.

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 128372-89-4, tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Article; He, Zhi-Tao; Wei, Ya-Bing; Yu, Hong-Jie; Sun, Cai-Yun; Feng, Chen-Guo; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 68; 45; (2012); p. 9186 – 9191;,
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.139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.Product Details of 139022-25-6

(5-(([2 ‘-Bipyridin]-3-yloxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (product of step-2, 0.320 g, 0.997 mmol) was reacted with imidazo[l,2- a]pyridine-6-carboxylic acid (0.193 g,1.197 mmol) in presence of BOP reagent (0.485 g, 1.096 mmol) and DIPEA (0.525 mL, 2.991 mmol ) in DMF (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulphate and concentrated under reduced pressure to get a residue. The residue was purified by combiflash column chromatography (dichloromethane/methanol/triethylamine = 91/8/1) to afford the title compound (0.150 g, 35%) as a solid. LCMS: nt/z 428.7 [M+H] +; HPLC: 97.93 % ; NMR (400 MHz, DMSO-de): delta 9.16 – 9.12 (d, / = 1.8 Hz, 1H), 9.11 (s, 1H), 9.05 – 8.99 (t, / = 5.5, 5.5 Hz, 1H), 8.61 – 8.54 (dt, / = 3.3, 1.5, 1.5 Hz, 1H), 8.37 – 8.31 (d, / = 4.5 Hz, 1H), 8.30 – 8.25 (m, 1H), 8.11 (s, 1H), 7.68 – 7.60 (m, 4H), 7.51 – 7.45 (dd, / = 7.9, 4.8 Hz, 1H), 7.45 – 7.39 (dd, / = 8.4, 4.6 Hz, 1H), 5.01 – 4.91 (dq, / = 10.4, 5.6, 5.6, 5.4 Hz, 1H), 4.28 – 4.12 (m, 4H), 3.27 – 3.15 (dd, / = 17.6, 11.2 Hz, 1H), 3.00 – 2.86 (dd, / = 17.7, 7.1 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem