Category: pyridine-derivatives

Synthetic Route of 5346-38-3 ,Some common heterocyclic compound, 5346-38-3, molecular formula is C6H6N2S, 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 25 mL N,N-dimethyl formamide (DMF) containing alpha-b r omo a c e t o p heno n e ( 1 . 1 g , 5 . 5 m m o l ) , 2-pyridinecarbothioamide (760 mg, 5.5 mmol) was added.After kept stirring for 24 h, the reaction mixture was diluted with 200 mL EtOAc followed by washing with brine. Theorganic layer was dried over anhydrous Na2SO4 and evaporatedunder reduced pressure. Separation through flash columnchromatography using a mixture of n-hexane andEtOAc as eluents provided a white solid as the product. Yield: 81.0 %. Mp: 72-73 C. IR (film, cm-1): 3111, 3057,1576, 1499, 1462, 1461, 1273, 1240, 1065, 993, 781, 740,683. 1H NMR (CDCl3, 300 MHz, ppm) delta = 7.37-7.39 (m,2H), 7.46-7.51 (m, 2H), 7.63 (s, 1H), 7.83-7.88 (m, 1H), 8.03(d, 2H, J = 7.0 Hz), 8.36 (d, 1H, J = 7.8 Hz), 8.58 (d, 1H,J = 4.6 Hz).13C NMR (CDCl3, 75 MHz, ppm) delta = 115.3,119.9, 124.5, 126.4, 128.2, 128.8, 134.5, 137.1, 149.5,151.5, 156.7, 168.8. Anal. Calcd. (%) for C14H10N2S: C70.56, H 4.23, N 11.76. Found: C 70.48, H 4.31, N 12.01.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5346-38-3, its application will become more common.

Reference:
Article; Yang, Ming-Yang; Zhao, Xiao-Long; Zheng, Ming-Hua; Wang, Yue; Jin, Jing-Yi; Journal of Fluorescence; vol. 26; 5; (2016); p. 1653 – 1657;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7464-14-4, 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.7464-14-4, name is 2-Hydroxy-5-methyl-3-nitropyridine, molecular formula is C6H6N2O3, molecular weight is 154.12, as common compound, the synthetic route is as follows.

(Reference Example 5-1) At room temperature, to a mixed solvent solution of 5-methyl-3-nitropyridin-2-ol (5.0 g) in tetrahydrofuran (200 ml) and methanol (200 ml) was added 10% palladium carbon (0.5 g), followed by stirring for 24 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and then the filtrate was concentrated under reduced pressure to afford 3-amino-5-methylpyridin-2-ol (4.03 g). 1H NMR (400 MHz, CDCl3) delta: 2.03(s, 3H), 4.11 (br s, 2H), 6.53 (s, 1H), 6.59 (s, 1H), 12.21 (br s, 1H).

Statistics shows that 7464-14-4 is playing an increasingly important role. we look forward to future research findings about 2-Hydroxy-5-methyl-3-nitropyridine.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-12-5, Adding some certain compound to certain chemical reactions, such as: 885588-12-5, name is 2-Bromo-5-fluoro-4-pyridinecarboxylic acid,molecular formula is C6H3BrFNO2, 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 885588-12-5.

To a solution of 2-bromo-5-fluoroisonicotinic acid (3.0 g, 13.64 mmol) in EtOH (30 mL) was added EtONa (3.7 g, 54.55 mmol). The reaction was heated at 60 00 for 24 hours then cooled to room temperature and thionyl chloride (3.2 g, 27.28 mmol) added dropwise. Thereaction was stirred at room temperature overnight then the solvent removed. The residue was partitioned between DOM (20 mL) and water (10 mL) and the aqueous phase extracted with DOM (3 x 10 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution (3 x 10 mL), brine (3 x 10 mL), dried (Na2SO4), filtered and concentrated. The residue obtained was purified by column chromatography(EtOAc/petroleum ether=1/20 v/v) to give the title compound (2.1 g, 56%) as an off-white solid. 1H-NMR (400MHz, ODd3) 6 8.14 (s, 1 H), 7.69 (s, 1 H), 4.40-4.35 (q, J = 7.2 Hz, 2H), 4.21-4.15 (q, J= 6.8 Hz, 2H), 1.46 (t, J= 7.2 Hz, 3H), 1.38 (t, J= 7.2 Hz, 3H); LOMS RT2.61 mm; m/z 274, 276 [M+H].

According to the analysis of related databases, 885588-12-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; BERGMAN, Ylva Elisabet; CAMERINO, Michelle Ang; STUPPLE, Paul Anthony; (81 pag.)WO2017/153520; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

A resealable pressure vessel was charged with tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate (1.54 g, 4.8 mmol), ((prop-2-yn-1-yloxy)methyl)benzene (0.84 g, 5.8 mmol), bis(triphenylphosphine) palladium(II) chloride (0.17g, 0.24 mmol), copper(I) iodide (0.09 g, 0.48mmol), triethylamine (15 mL, 108 mmol) and DMF (5 mL). The mixture was degassed by bubbling nitrogen through for several minutes, the flask was sealed and the reaction mixture was stirred for 7h.. The mixture was diluted with EtOAc and washed with saturated ammonium chloride (2x) and brine (1x). The organics were dried over sodium sulfate, filtered and evaporated, and the crude material purified by silica gel chromatography, eluting with 12-100% EtOAc in hexanes, affording tert-butyl (4-(3-(benzyloxy)prop-1-yn-1-yl)pyridin-3-yl)carbamate (1.6 g, 98%). 1H NMR (400MHz, CHLOROFORM-d) delta = 9.44 (s, 1H), 8.28 (d, J=4.8 Hz, 1H), 7.45 – 7.33 (m, 5H), 7.26 (d, J=4.8 Hz, 1H), 7.14 – 6.93 (m, 1H), 4.71 (s, 2H), 4.50 (s, 2H), 1.56 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McDonald, Ivar M.; Mate, Robert; Ng, Alicia; Park, Hyunsoo; Olson, Richard E.; Tetrahedron Letters; vol. 59; 8; (2018); p. 751 – 754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59281-14-0, 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.59281-14-0, name is 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, molecular formula is C13H13NO3, molecular weight is 231.25, as common compound, the synthetic route is as follows.

General procedure: 20 mmol of compound 4 (4a-4f) was weighed into 100 mL of dichloromethane, Then add 0.16 mol of manganese dioxide, The mixed system was heated under reflux at 50 C in a oil bath for 72-96 h, and the TLC spot plate was used to detect the reaction process. After the reaction is over, The manganese dioxide was removed by suction filtration and the solvent 5 was evaporated to give compound 5.

Statistics shows that 59281-14-0 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one.

Reference:
Patent; Zhejiang Gongshang University; Zhou Tao; Shao Lele; (12 pag.)CN106986819; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 207799-10-8, 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. 207799-10-8, name is tert-Butyl (4-bromopyridin-2-yl)carbamate, molecular formula is C10H13BrN2O2, 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.

tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of ter/-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0C is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 muL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound. Yield: 240 mg (76%). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).

According to the analysis of related databases, 207799-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; CURIS, INC.; WO2008/57469; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13472-85-0, 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.13472-85-0, name is 5-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

A 2.5 M hexane solution of n-butyllithium (23 mL, 58 mmol) was added over 30 minutes to a -78 C. solution of 5-bromo-2-methoxypyridine (10 g, 53 mmol) in ether (120 mL), keeping the temperature below -65 C. The slurry was stirred for 30 minutes, and then trimethylborate (6.1 mL) was added quickly to the reaction solution. Again the temperature was maintained below -65 C. The solution was stirred for 10 minutes, warmed to 15 C. and then cooled to -78 C. Peracetic acid (56 mmol) was added dropwise, while the temperature was kept at or below -65 C. After addition, the reaction was warmed briefly to -50 C., cooled back to -65 C., then stirred at approximately 25 C. overnight. The reaction was quenched with water (100 mL), and then extracted with ether (3*150 mL). The organic portions were combined and washed with aqueous NaHSO3 solution and brine. The organic portions were extracted two times with 2N aqueous NaOH solution. The pooled basic aqueous fractions were washed with Et2O and then acidified with NaHSO4. The product precipitated out as oil; the aqueous mixture was extracted three times with Et2O, the pooled ether fractions were dried with Na2SO4, and stripped of solvent in vacuo. Yielded 3.6 g of a brown solid.

The chemical industry reduces the impact on the environment during synthesis 13472-85-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Brewster, William Kirkland; Klittich, Carla Jean Rasmussen; Balko, Terry William; Breaux, Nneka Tuere; Erickson, William Randal; Hunter, James Edward; Lowe, Christian Thomas; Ricks, Michael John; Siddall, Thomas Lyman; Yerkes, Carla Nanette; Zhu, Yuanming; US2006/89370; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 770-08-1, 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. 770-08-1, name is 5-Ethylpicolinic acid, molecular formula is C8H9NO2, 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 IV; Preparation of [1-(6-trichloromethylpyridin-3-yl)ethyl](methyl)-oxido-lambda4-sulfanylidenecyanamide (5); A mixture of 5-ethylpyridine-2-carboxylic acid (1.98 g, 13 mmol), phenyl-phosphonic dichloride (2.8 g, 14.3 mmol), phosphorus pentachloride (7.7 g, 32 mmol) was stirred and slowly heated. Once a clear yellow liquid was formed, the mixture was heated to reflux overnight. After cooling, the volatiles were removed under reduced pressure. The residue was carefully poured into saturated sodium carbonate aqueous solution cooled in an ice-water bath. The aqueous phase was then extracted with CH2Cl2 two times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated, and partially purified on silica gel eluted with 10 percent EtOAc in hexane to give 2.7 g of crude product containing both 5-ethyl-2-(trichloromethyl)pyridine and 5-(1-chloro-ethyl)-2-(trichloromethyl)pyridine in an approximate 3:1 ratio (GC data, masses calcd for C8H8Cl3N and C8H7Cl4N [M]+223 and 257 respectively. Found 223 and 257 respectively).

According to the analysis of related databases, 770-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences, LLC; US2010/168177; (2010); 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride. A new synthetic method of this compound is introduced below., Formula: C7H8ClNO2

To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0 C was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0 C for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95%) was used in the next step without further purification.

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, 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; KEANEY, Gregg F.; WANG, John; GERARD, Baudouin; ARAI, Kenzo; LIU, Xiang; ZHENG, Guo, Zhu; KIRA, Kazunobu; TIVITMAHAISOON, Parcharee; PRAJAPATI, Sudeep; GEARHART, Nicholas C.; KOTAKE, Yoshihiko; NAGAO, Satoshi; KANADA SONABE, Regina, Mikie; MIYANO, Masayuki; MURAI, Norio; BUONAMICI, Silvia; YU, Lihua; PARK, Eunice, Sun; CHAN, Betty; SMITH, Peter, G.; THOMAS, Michael P.; PAZOLLI, Ermira; LIM, Kian, Huat; (54 pag.)WO2017/87667; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 162102-79-6, 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 162102-79-6 as follows.

To a solution of dimethyl 4-bromopyridine-2,6-dicarboxylate (CAS 162102-79-6) (2.40 g, 8.8 mmol, 1.0 eq) in MeOH/DCM solution (10/1, 88 mL) was added KOH (896 mg, 8.0 mmol, 0.9 eq) at rt. The reaction mixture was stirred at rt for 3 h and Et20 (80 mL) was added thereto. The resulting white solid was filtered and then redissolved in water (50 mL). 2 M HC1 solution (8 mL) was added. The mixture extracted with DCM (2 x 50 mL). The combined organic layers were washed with brine and dried over anhydrous Na2S04. After removing the solvent, the residue as brown solid was used directly in the next step without further purification (1.0 g, Y: 44%). ESI-MS (M+H) +: 259.9. 1H NMR (400 MHz, CDC13) delta: 8.56 (d, J = 1.7 Hz, 1H), 8.50 (d, J = 1.7 Hz, 1H), 4.04 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162102-79-6, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; CHAN, Timothy; GUCKIAN, Kevin; JENKINS, Tracy; THOMAS, Jermaine; VESSELS, Jeffery; KUMARAVEL, Gnanasambandam; MEISSNER, Robert; LYSSIKATOS, Joseph; LUCAS, Brian; LEAF, Irina; DUFFIELD, Jeremy; (518 pag.)WO2016/11390; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem