Category: pyridine-derivatives

Related Products of 13603-44-6, 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. 13603-44-6, name is 2,6-Dimethylpyridin-4-ol. A new synthetic method of this compound is introduced below.

2,6-Dimethyl-pyridin-4-yl trifluoromethanesulfoiiate (91)A suspension of pyridone 90 (5.0 g, 40.6 mmol) in DCM (100 mL) at O0C was treated with triethylamine (8.50 mL, 60.9 mmol) followed by trifluoromethane- sulfonic anhydride (10.2 mL, 60.9 mmol), added dropwise via syringe over 5 minutes. After warming to RT and stirring 2 h, the reaction mixture was washed with aqueous NaHCO3 (3 x 100 mL) and reduced in vacuo to afford the title compound.Yield: 9.25 g (quant.).LC/MS ttau 0.96 min.MS(ES+) m/z 256 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13603-44-6, 2,6-Dimethylpyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; WO2007/89669; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-91-8, 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]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, Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine

5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine (235 mg) was dissolved in dichloromethane (5 ml). Di-tert-butyl dicarbonate (248 mg) and N,N-dimethylaminopyridine (1.2 mg) were added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (297 mg).MS (ESI) m/z: 331 (M+H)+.1H-NMR (CDCl3) delta: 1.67 (9H, s), 7.65 (1H, s), 8.05 (1H, d, J=2.2 Hz), 8.58 (1H, d, J=2.2 Hz).

The synthetic route of 951626-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-78-7, 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. 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. A new synthetic method of this compound is introduced below.

(2) Synthesis of 2-fluoro-4-iodo-3,5-dimethylpyridine Diisopropylamine (88 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. in a nitrogen atmosphere. A 2.69 M solution of n-butyllithium in hexane (215 mL) was added dropwise to the solution. After completion of the dropwise addition, the mixture was warmed to -5 C. with stirring over 30 minutes. The reaction mixture was cooled to -72 C. A solution of 2-fluoro-3-iodo-5-methylpyridine (109.69 g) in TIE (240 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -74 C. for 1.5 hours. A solution of methyl iodide (36 mL) in THF (160 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -70 C. to -74 C. for two hours. After completion of the reaction, water (200 mL) was added to the reaction mixture at the same temperature. The mixture was stirred at the same temperature for two minutes. The reaction mixture was returned to room temperature, and water (1.2 L) was then added. The mixed solution was stirred for three minutes. Water (300 mL) was further added. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. n-heptane (100 mL) was added to the residue, followed by cooling. The precipitated solid was collected by filtration. The residue was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. This operation was repeated twice to give the title compound (86.9 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.39-2.40 (m, 6H), 7.80-7.82 (m, 1H). ESI-MS m/z 252 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-78-7, 2-Fluoro-3-iodo-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6602-32-0, 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 6602-32-0 as follows.

Synthesis of T131 proceeded from the known intermediate 131-3 (Schlosser, M. et. al. Tetrahedron 2005, 61, 717-725) via the multi-step sequence illustrated. For the key RCM step, either Grubb’s second generation catalyst (Ru-1) or the Grubbs-Hoveyda catalyst (Ru-2) could be employed. The yield for the synthesis of 131-8 was complicated by concurrent elimination side reaction. In order to avoid this, an alternative synthetic route conducting the RCM prior to the displacement reaction can be employed.1H NMR (CDCl3, 300 MHz): delta 7.97 (d, J=4.7, 1H), 6.84 (d, J=5.0, 1H), 5.02 (s, br, 1H), 4.14 (m, 1H), 3.83 (m, 2H), 3.13 (m, 2H), 2.80 (m, 5H), 1.90 (m, 4H), 1.44 (s, 9H)13C NMR (CDCl3, 75 MHz): delta 156.14, 150.12, 149.36, 140.12, 129.59, 122.20, 79.19, 77.20, 65.19, 40.13, 29.42, 28.42, 28.24, 24.06, 22.94MS: 323 (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,6602-32-0, its application will become more common.

Reference:
Patent; Tranzyme Pharma Inc.; US2008/194672; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13091-23-1, 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 13091-23-1 as follows.

Ammonia (74.0 mL, 3418.64 mmol) was condensed into THF (170 mL) cooled to -78 0C under nitrogen. Potassium tert-butoxide (23.98 g, 213.67 mmol) was added as a solid and the reaction mixture warmed to -35 0C. tert-Butyl hydroperoxide (5.5 M soln. in decane) (16.32 mL, 89.74 mmol) was added dropwise to 4-chloro-3-nitropyridine (13.55 g, 85.47 mmol) in THF (200 mL) cooled to 0 0C over a period of 5 minutes under nitrogen. The resulting solution was added slowly to the other flask and the mixture stirred at -35 0C for 1.5 hours. The reaction mixture was quenched with saturated NH4CI (50 mL) and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the brown precipitate filtered and washed with cold water to yield crude product. The solid was dried overnight under vacuum to yield 4-chloro-5-nitropyridin-2-ol (14.66 g, 83.99 mmol, 98 %) as a yellow solid. 1R NMR (400 MHz, DMSO) delta 6.36 (IH, s), 8.73 (IH, s). m/z 173 (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,13091-23-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58584-92-2, 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 58584-92-2 as follows.

2-Amino-6-chloronicotinamide (Inter. 3) To a 0.3 M solution of 2-amino-6-chloronicotinic acid (Inter. 2) (1 equiv) in anhydrous THF, under an inert atmosphere, was added thionyl chloride (3.3 equiv) in a dropwise fashion. The reaction mixture was stirred at room temperature for 2 hours. After this time the reaction was concentrated in vacuo to give a crude yellow solid residue. The crude solid was dissolved in THF (equal to initial reaction volume) and concentrated in vacuo again to give a yellow solid residue. The residue was dissolved once more in THF and concentrated as before to give a solid residue which was then dissolved in THF (to give a solution of 0.3M) and ammonia gas bubbled through the solution for 1 hour. The resultant precipitate was removed by filtration and the filtrate concentrated in vacuo to give a yellow precipitate which was triturated with water at 50 C. then dried to give the title compound (92% yield, 93% purity), suitably clean to be used without any further purification. m/z (LC-MS, ESP): 172 [M+H]+R/T=3.19 mins

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-92-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2009/99174; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic 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, 52833-94-0, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5BrN2O2

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4C1 (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, suspended in water and extracted with CH2C12. The organic layer was washed with brine, dried over Na2S04 and concentrated to give the product of 2-amino-5- bromonicotinamide (1.80 g, yield: 80%), which was used for the next step without further purification. NMR (DMSO-i, 400 MHz) delta 8.14 (dd, J= 4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H)+: 216 / 218.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52833-94-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-hydroxypyridine

To a solution of 2-chloropyridin-4-ol (1 g, 7.75 mmol) in DMA (10 ml) was added bromocyclopropane (2.8 g, 23.2 mmol), Nal (1.16 g, 7.75 mmol) and CS2CO3 (5 g, 15.5 mmol). The mixture was stirred at MW 170 C for 20 minutes, and then MW 180 C for 30 minutes. The reaction mixture was extracted with EA. The organic layer was dried and concentrated. The residue was purified by flash column chromatography to give 300 mg of 2-chloro-4-cyclopropoxypyridine. 1H NMR (400MHz, CDC13 ) delta = 8.19 (d, J=5.8 Hz, IH), 7.02 (d, J=2.0 Hz, IH), 6.87 (dd, J=2.0, 5.8 Hz, IH), 3.80 (tt, J=3.0, 6.0 Hz, IH), 0.91 – 0.75 (m, 4H)

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, 17368-12-6, 2-Chloro-4-hydroxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5345-47-1 ,Some common heterocyclic compound, 5345-47-1, molecular formula is C6H6N2O2, 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.

2-Amino-nicotinic acid (2 g, 14.48 mmol) was dispersed in glacial acetic acid. To this suspension was added a solution of bromine (1.2 mL) in glacial acetic acid (5 mL). The mixture was stirred at room temperature for 20 h. The mixture was filtered and washed with glacial acetic acid (10 mL) and water in several portions. The precipitate was collected and dried to give 2-amino-5-bromonicotinic acid (3.0 g, 95 % yield) as yellow solid. XH-NMR (DMSO- d6, 400 MHz) delta 8.31 (d, J= 2.4 Hz, 1H), 8.18 (d, J= 2.8 Hz, 1H), 5.06-5.27 (m, 2H). MS (M+H)+: 218 / 220.

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. 5345-47-1, 2-Aminonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113118-81-3, 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. 113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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: Steps 1 To a solution of 5-bromopyridin-3-amine (XIX) (535 mg, 3.09 mmol) in MeOH (62 mL) was added acetone (296 muL, 4.02 mL). The pH was adjusted to 4 using HOAc and stirred for 30 min. NaCNBH3 (272 mg, 4.33 mmol) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% hexane?90:10 hexane:EtOAc) to produce 5-bromo-N-isopropylpyridin-3-amine (XXXVII) as an oil which slowly solidified into an off-white solid (309 mg, 1.44 mmol, 47% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.12 (d, J=6.3 Hz, 6H), 3.55-3.59 (m, 1H), 6.03 (d, J=7.9 Hz, 1H), 7.05-7.06 (m, 1H), 7.75 (d, J=2 Hz, 1H), 7.90 (d, J=2 Hz, 1H); ESIMS found C8H11BrN2 m/z 215.1 (M+H).

According to the analysis of related databases, 113118-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (262 pag.)US2016/68547; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem