Category: pyridine-derivatives

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 941294-57-1, name is 5-Bromo-2-iodo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5BrIN

Step B: 5-Bromo-4-methyl-pyridine-2-carbaldehyde In an oven-dried flask the compound obtained in Step A (4.67 g) was dissolved in tetrahydrofuran (22 ml). The solution was cooled to -15 C., then isopropyl magnesium bromide (17.2 ml, 15% solution in THF) was added dropwise at a rate to keep the internal temperature between -15 C. to -10 C. The reaction was stirred at this temperature for 1 hour, then anhydrous dimethylformamide (1.8 ml) was added at a rate to keep the internal temperature below 0 C. The reaction was stirred at this temperature for 1 hour, then poured into water and extracted with diethyl ether. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude title aldehyde product (2.4 g, brown solid) was used as such in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 941294-57-1.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); 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.147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.Formula: C6H5F3N2

1,3-cyclopentanedione (3.3 g, 33.9 mmol) and 4-amino-2-trifluoromethylpyridine (5.0 g, 30.8 mmol) are suspended in acetic acid (15 mL) and shaken at 130 C under microwave irradiation overnight. The reaction mixture is diluted with water and purified by reversed phase HPLC. Yield: 4.17 g; ESI mass spectrum [M+H]+=243; Retention time HPLC: 0.77 min (method Z018_S04).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; PETERS, Stefan; ANDERSKEWITZ, Ralf; GNAMM, Christian; HOESCH, Holger; MORSCHHAEUSER, Gerd; OOST, Thorsten; RIES, Uwe Joerg; (84 pag.)US2016/31830; (2016); 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.82671-02-1, name is 2,6-Dichloro-5-fluoronicotinonitrile, molecular formula is C6HCl2FN2, molecular weight is 190.99, as common compound, the synthetic route is as follows.Recommanded Product: 2,6-Dichloro-5-fluoronicotinonitrile

Weigh 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (24.8 g, 130 mmol)Concentrated sulfuric acid (125 mL) was added to a 500 ml flask, and the mixture was heated to 62 C for 1 hour.After cooling to room temperature, the reaction solution was poured into ice water (800 mL) and ethyl acetate (300 mL×4).The organic phase was washed successively with water (100 mL), saturated sodium bicarbonate (100 mL) and brine (50 mL).Dry over anhydrous sodium sulfate.Filtered, the filtrate was dried,A pale yellow solid (27.0 g, 99.5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,82671-02-1, 2,6-Dichloro-5-fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ·geerdeman; (79 pag.)CN108690016; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 881-86-7, 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. 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, 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.

To a mixture of dimethyl pyridine-2,5-dicarboxylate (3.08 g, 15.78 mmol) and calcium chloride (7.01 g, 63.1 mmol) in tetrahychofuran (33 mL) and EtOH (67 mL) was added sodium borohydride (1.493 g, 39.5 mmol) in portions at 0 C. The reaction mixture was stirred at 0 C for 12 hrs. The mixture was poured into ice/water, was diluted with dichloromethane (400 mL) and stirred vigorously for 15 minutes. The separated organic layer was dried over magnesium sulfate, filtered off and concentrated under reduced pressure providing methyl 6-(hydroxymethyl)nicotinate (1.2 g) as an off white solid, which was directly used in the next step without further purification. LCMS (m/z): 168.0 [M+H]+; Rt = 0.26 min

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 881-86-7, Dimethyl pyridine-2,5-dicarboxylate.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

4-Chloro-3-nitropyridin-2-amine (500 mg, 2.89 mmol) and 4-amino-2-fluorophenol (403.8 mg, 3.18 mmol) were mixed in dry DMF (10 mL), and t-BuOK (356.1 mg, 3.18 mmol) was added. This mixture was heated to 80 C under N2 for 1 h, then cooled to room temperature. Water (50 mL) was added to quench the reaction, and the mixture was extracted with EA (3 × 50 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated in vacuum, and purified by column chromatography to yield the corresponding ether 20b (618.0 mg, 81%). 1H NMR (300 MHz, DMSO) delta 7.95 (dd, J = 5.8, 0.7 Hz, 1H), 6.96 (t, J = 8.7 Hz, 1H), 6.54 – 6.40 (m, 2H), 6.15 (s, 2H), 6.03 (dd, J = 5.7, 1.3 Hz, 1H), 3.80 (s, 2H). EI-MS m/z: 264 (M)+.

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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; An, Xiao-De; Liu, Hongyan; Xu, Zhong-Liang; Jin, Yi; Peng, Xia; Yao, Ying-Ming; Geng, Meiyu; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry Letters; vol. 25; 3; (2015); p. 708 – 716;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 105170-27-2, Adding some certain compound to certain chemical reactions, such as: 105170-27-2, name is 2-Bromo-5-methoxypyridine,molecular formula is C6H6BrNO, 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 105170-27-2.

Example 287A [1-(3,4-dichlorophenyl)cyclobutyl](5-methoxypyridin-2-yl)methanone A solution of 2.5M n-Butyl lithium (6.5 mL, 16.25 mmol) in hexanes plus anhydrous diethyl ether (50 mL) was chilled to -75 C., followed by the dropwise addition of 2-bromo-5-methoxypyridine (3.12 g, 16.59 mmol) in diethyl ether (5 mL). The brown solution was stirred for 1 hour, followed by the addition of 1-(3,4-dichlorophenyl)-cyclobutanecarbonitrile (3.0 g, 13.27 mmol) in diethyl ether (5 mL). The reaction was warmed to 0 C. while stirring for 2 hours. The reaction was quenched with 1N hydrochloric acid (100 mL) and the biphasic mixture was stirred for 1 hour at ambient temperature. Added 3N sodium hydroxide (100 mL) and extracted twice with EtOAc (200 mL). The combined organic phases was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (0-100% EtOAc in heptane) to give Example 287A (4.046 g, 12.03 mmol, 91% yield) as a light yellow oil. MS (ESI+): m/z 336 (M+H). 1H NMR (500 MHz, CD3CN) delta 8.14 (d, J=2.9 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.64 (d, J=2.1 Hz, 1H), 7.40 (d, J=8.3 Hz, 1H), 7.35 (dd, J=8.4, 2.1 Hz, 1H), 7.31 (dd, J=8.8, 2.9 Hz, 1H), 3.86 (s, 3H), 3.00-2.89 (m, 2H), 2.66-2.54 (m, 2H), 2.02-1.91 (m, 1H), 1.89-1.77 (m, 1H).

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. 105170-27-2, 2-Bromo-5-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 136117-74-3, Imidazo[1,2-a]pyridine-8-carbaldehyde, 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, 136117-74-3, blongs to pyridine-derivatives compound. Formula: C8H6N2O

[0167] To a solution of dimethyl 3-oxo-l ,3-dihydroisobenzofuran-l-ylphosphonate (610 mg, 2.4 mmol), imidazo[l,2-a]pyridine-8-carbaldehyde (350 mg, 2.4 mmol, lequiv.) in THF ( 5 mL) was added Et3N (0.33 mL 2.4 mmol). The mixture was stirred at rt for 48 h. The precipitation was filtered off and washed with EtOAc. The filtrate was concentrated to give 3-(imidazo[l,2-a]pyridin-8-ylmethylene)isobenzofuran-l(3H)-one(400 mg, 64%>) as a yellow solid. Small crude sample (-20 mg ) was purified on RP-HPLC with CCN and water as eluent to separated the E/Z isomers (10 mg, 7 mg). NMR(400 MHz, CD3OD) Z-form: delta= 8.52 (d, 1 H), 7.95-7.91 (m, 2 H), 7.62-7.54 (m, 4 H), 7.52-7.48 (m, 1 H), 7.09 (s, 1 H), 7.04 (t, 1 H) E-form: delta= 8.38 (d, 1 H), 8.15 (d, H), 8.05 (d, 1 H), 7.95 (d, 1 H), 7.90-7.84 (m, 2 H), 7.67 (t, 1 H), 7.64 (s, 1 H), 7.33 (s, 1 H), delta 7.05 (t, 1 H). LRMS (M+H+) m/z 263.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,136117-74-3, its application will become more common.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102142; (2013); 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.113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of diisopropylamine (345 mL, 249 g, 2.46 mol) in anhydrous THF (5 L) at -8 to -10 C. under a blanket of N2 was added n-BuLi (880 mL, 158 g, 2.46 mol) dropwise via cannula. The mixture was stirred at -10 C. for 30 min, cooled to -78 C. and treated with a solution of 2-fluoro-3-iodopyridine (500 g, 2.24 mol) in dry THF (2 L) dropwise. After the addition, the reaction mixture was warmed to -60 C. and this temperature was maintained for 2 h. The mixture was then cooled to -78 C., treated with ethyl formate (183 g, 2.47 mol) dropwise, followed by sodium methoxide (149 g, 2.75 mol) in MeOH (1.5 L) and warmed to ambient temperature. The reaction mixture was quenched with ice water and extracted with EtOAc. The layers were separated and the organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 4-iodo-2-methoxynicotinaldehyde (380 g, 64%) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113975-22-7, 2-Fluoro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/114033; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, 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, Computed Properties of C7H5NOS, blongs to pyridine-derivatives compound. Computed Properties of C7H5NOS

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-5-methanesulfonyl-2,3-dihydrobenzofuran (100 mg) and thieno[3,2-b]pyridin-7-ol (82.9 mg) in 0.75 mL of anhydrous ethanol was added sodium ethoxide (21 wt. % solution in ethanol, 102 muL). After heating at 85 C. for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 4% methanol-methylene chloride) to give the title compound as a pale yellow solid (108 mg), m.p. 163 C.-165 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2005/234091; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5470-22-4, 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 5470-22-4 as follows.

Compound 5 was prepared according to a modified procedure (WO2013/057253). To a suspension of the commercially available 4-chloro-pyridine-2-carboxylic acid 4 (5.0 g, 31.84 mmol) in dichloromethane (135 ml) at 0 C was added oxalyl chloride (4.8 g, 38.21 mmol), followed by a slow addition of catalytic amount of dimethylformamide (0.55 ml). The resulting mixture was stirred at room temperature for 2 h. After this time, the mixture was concentrated to dryness under reduced pressure. The solid residue was solubilized in methanol (55 ml) and was stirred at room temperature for another 16 h. The mixture was concentrated to dryness under reduced pressure, and the residue re-suspended with 5% aq. NaHCC>3. The product was extracted with EtOAc (2 x 20 ml). The combined organic layer was washed with brine (2 chi 10 ml), dried over anhydrous MgS04, filtered and concentrated to dryness under reduced pressure to afford 5 (4.0 g, 74%) as a beige solid. XH N MR (300 M Hz, CDCI3): delta 8.63 (d, J = 5.0 Hz, 1H), 8.12 (dd, J = 2.0, 0.5 Hz, 1H), 7.48 (dd, J = 5.0, 2.0 Hz, 1H), 4.00 (s, 3H). 13C N MR (75 MHz, CDCI3): delta 164.7, 150.7, 149.3, 145.5, 127.2, 125.7, 53.3. HRMS (APPI) calcd. for C7H7CI N02+ [M+H]+ 172.0160, found: 172.0156.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-22-4, its application will become more common.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT CURIE; UNIVERSITY OF TEXAS AT AUSTIN; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE; RODRIGUEZ, Raphael; ZACHARIOUDAKIS, Emmanouil; KUNALINGAM, Lavaniya; BARTOLI, Alexandra; MILLER, Kyle; AGARWAL, Poonam; (41 pag.)WO2017/102934; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem