Month: September 2021

Electric Literature of 1033201-61-4, 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 1033201-61-4 as follows.

A slurry of 6-amino-3-bromopicolinic acid (25 g) in 400 mL 1:1 dichloromethane/chloroform was added to nitrosonium tetrafluoroborate (18.2 g) in dichloromethane (100 mL) at 5 C. over 1 hour. The resulting mixture was stirred for another 30 minutes, warmed to 35 C., and stirred overnight. The reaction mixture was cooled to room temperature and adjusted to pH 4 with a NaH2PO4 solution. The resulting solution was extracted three times with dichloromethane, and the combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1033201-61-4, its application will become more common.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 148493-37-2, 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. 148493-37-2, name is 2,6-Dichloro-3-iodopyridine, molecular formula is C5H2Cl2IN, 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 1 necked round bottom flask, with stirrer, and air condenser, under nitrogen, is added 2,6-dichloro-3-iodo-pyridine (1.0 g, 3.8 mmol), 2- [(E)-2-ethoxyvinyl]-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.9 g, 4.8 mmol), CS2CO3 (3.75 g, 11.5 mmol), l,4-dioxane (19.2 mL), and water (4.26 mL). This reaction mixture is purged 3 times alternating between vacuum and nitrogen, and [l,T bis(diphenylphosphino) ferrocene]dichloropalladium(II) (0.2 g) is added. The resulting mixture is stirred for 3 hr at 90 C, the reaction is poured onto saturated aqueous NH4Cl, and the aqueous mixture is extracted three times with EtOAc. The combined organic extracts are dried over MgS04, filtered, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by flash chromatography over silica gel, eluting with a gradient of 0-100% EtOAc in cyclohexane, to afford the title compound (748 mg, 89% yield), after solvent evaporation of the desired chromatographic fractions. NMR (300 MHz, CDCh): d 1.37 (m, 3H), 3.97 (m, 2H), 5.97 (m, 1H), 6.99 (m, 1H), 7.16 (m, lH),7.60 (m, 1H).

According to the analysis of related databases, 148493-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; DREYFUS, Nicolas Jacques Francois; FALLER, Andrew; (44 pag.)WO2019/245907; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, 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 C9H8BrNO4, blongs to pyridine-derivatives compound. Computed Properties of C9H8BrNO4

In a sealed tube, a mixture of 1 (2.74 g, 10 mmol)and (S)-phenylalaninol (3.78 g, 25 mmol) in methanol (10 mL) was stirred at 115 C for 12 h. After cooling to ambient temperature, the crude product was poured into crushed ice (100 g), stirred for15 min, filtered, washed with water (20 mL 3) and the residues was dried under vacuum. The white product was used for the next step without further purification (4.50 g, 88%). 1H NMR (400 MHz,CDCl3): d 8.43 (s, 2 H), 7.94 (d, J 8 Hz, 2 H), 7.32e7.21 (m, 10 H),4.40e4.32 (m, 2 H), 3.83e3.74 (m, 4 H), 3.06e2.96 (m, 4 H), 2.59 (br,2 H). 13C NMR (150 MHz, CDCl3): d 162.6, 149.7, 137.5, 136.4, 129.4,128.8, 128.5, 126.9, 63.6, 53.1, 37.0. HRMS (MALDITOF) calcd forC25H27BrN3O4 [M H] 512.1179, found 512.1186.

The synthetic route of 162102-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ya-Qi; Pan, Yao; Gao, Wan-Qing; Wu, Yuan; Liu, Chun-Hua; Zhu, Yuan-Yuan; Tetrahedron; vol. 75; 28; (2019); p. 3809 – 3814;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 152126-31-3, Adding some certain compound to certain chemical reactions, such as: 152126-31-3, name is 3-Fluoropicolinic acid,molecular formula is C6H4FNO2, 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 152126-31-3.

To 3-fluoro-2-pyridinecarboxylic acid (available from Fluorochem, 63mg, 0.44mmol) was added O-(7-azabenzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluronium hexafluorophosphate (172mg, 0.45mmol), DIPEA (0.106ml) and DMF (1 ml). The reaction was stirred for 20mins at 250C. 6-(1 H-indol-4-yl)-1 H-indazol-4-amine (50mg, 0.20mmol) was added and the reaction was stirred for a further 2Oh at 250C. The solvent was dried under a stream of nitrogen to give the crude product. This sample in DMF was loaded onto an aminopropyl cartridge (5g) and after standing for 3h, the column was washed with 10% methanol in dichloromethane. The appropriate fractions were combined and dried under a stream of nitrogen to give the crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). The solvent was dried under a stream of nitrogen to give the title compound (23mg). LCMS (Method B) R1 = 0.94mins, MH+ = 372

According to the analysis of related databases, 152126-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147190; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1231930-25-8, 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.1231930-25-8, name is 1-((6-Bromopyridin-3-yl)methyl)-4-ethylpiperazine, molecular formula is C12H18BrN3, molecular weight is 284.2, as common compound, the synthetic route is as follows.

A solution of 1- (6-bromo-pyridin-3-ylmethyl) -4-ethyl-piperazine (960 mg, 3.38 mmol) in anhydrous tetrahydrofuran (8 mL)Was added 2- (dicyclohexylphosphino) biphenyl (120 mg, 0.338 mmol)Tris (dibenzylideneacetone) dipalladium (154 mg, 0.169 mmol).Lithium hexamethyldisilazide (4.06 mL, 1 M, 4.06 mmol) was slowly added under nitrogen.The reaction flask was heated to 65 C,After 20 minutes the reaction flask was cooled to room temperature,50 mL of ethyl acetate was added,30mL water,Mixed after the liquid,The aqueous layer was again added with 30 mL of ethyl acetate,Liquid separation,Combined organic layer,Dried over anhydrous sodium sulfate and evaporated to dryness as a pale brown solid.The product of formula V-1 (670 mg) was purified by column chromatography,As a pale yellow solid.

The chemical industry reduces the impact on the environment during synthesis 1231930-25-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Zhang, Yinsheng; Liu, Yingshuai; Li, Li; Miao, Lei; Xu, Tongjie; Liu, Haiyan; Ma, Xueqin; Yu, Sen; Xu, Hongjiang; (49 pag.)CN106467517; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)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: 1123194-98-8, blongs to pyridine-derivatives compound. Recommanded Product: 1123194-98-8

DMF (52mL) was added to 6-Bromo-2-methoxy-3-(4-methyl-l H- imidazol-1-yl)pyridine (13.Og, 48.5mmol) and the tert-Butyl 2- acryloylhydrazinecarboxylate (9,9g, 53.3mmol) at room temperature under nitrogen atmosphere, And the mixture was stirred at 50C for 10minutes, Tri(o-tolyl)phosphine (885mg, 2.90mmol), Palladium (II) acetate (327mg, 1.45mmol) and N,N- diisopropylethylamine (12.7mL, 72.7mmol) were added to the mixture, and the reaction mixture was stirred at 100C for 4hours. The reaction mixture was cooled to room temperature and filtrated through Celite. The residue was washed twice with DMF (6mL). Water (104mL) was added dropwise to the filtrate at room temperature over lOminutes. The mixture was stirred at room temperature for l5hoursAfter the mixture was filtrated, the residue was washed with water/DMF =2; 1(3OmL) and MTBE (3OmL). The obtained solid was suspended in MTBE (5OmL) at room temperature for 2hours, filtrated and dried under the reduced pressure to obtain the title compound (15.8g, 87% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; NAKAMURA, Taiju; MATSUDA, Masaaki; HU, Yongbo; HASEGAWA, Daiju; HOSHINO, Yorihisa; INANAGA, Kazato; ISOMURA, Minetaka; SATO, Nobuaki; YOSHIZAWA, Kazuhiro; MONIZ, George A.; WILKIE, Gordon D.; FANG, Francis G.; NISHIKAWA, Yoshihiro; WO2010/25197; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6959-47-3, 2-(Chloromethyl)pyridine hydrochloride, 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, Quality Control of 2-(Chloromethyl)pyridine hydrochloride, blongs to pyridine-derivatives compound. Quality Control of 2-(Chloromethyl)pyridine hydrochloride

A mixture of 4 (0.8 g, 5.0 mmol), sodium carbonate (2.4 g, 22.6 mmol) and 2-pyridylmethyl chloride hydrochloride (1.8 g, 10.9 mmol) in 15 mL of dry ethanol was refluxed for 12 h under N2, and then evaporated. The residue was dissolved in 50 mL of aqueous solution of sodium hydroxide and extracted with dichloromethane (3 × 30 mL). Then the organic layer was dried over potassium carbonate and evaporated. The residue was separated by silica gel flash chromatography using EtOAc as eluent to give N-(2-(bis(2-pyridylmethyl)amino)ethyl)carbamic acid tert-butyl ester 5 (1.5 g, 91%) as yellow viscous oil. 1H NMR (400 MHz, CDCl3): delta 8.52 (d, 2H, J = 4.8 Hz), 7.60 (ddd, 2H, J = 7.2 Hz), 7.39 (d, 2H, J = 7.6 Hz), 7.12 (m, 2H), 5.82 (s, 1H), 3.85 (s, 4H), 3.21(m, 2H), 2.67 (t, 2H, J = 5.6 Hz), 1.43 (s, 9H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6959-47-3, 2-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Yan, Liwei; Ye, Zhongbin; Peng, Chunxiang; Zhang, Shihong; Tetrahedron; vol. 68; 12; (2012); p. 2725 – 2727;,
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. 5435-54-1, name is 3-Nitropyridin-4-ol. A new synthetic method of this compound is introduced below., Safety of 3-Nitropyridin-4-ol

To a suspension of 3-nitropyridin-4-ol (4.342 g, 31 mmol) in toluene (60 mL) was added POCl3 (11.6 mL, 124.4 mmol) at 0 C. The resulting mixture was warmed to room temperature, then heated to 110 C. for 14 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was poured into ice, and basified with saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc (40 mL×2). The combined organic layers was washed with water, brine, dried (MgSO4) and concentrated to a brown oil, which solidified on standing. (3.68 g, 75% yield).1H NMR (DMSO-d6): delta ppm 9.23 (s, 1H), 8.80 (d, J=5.4 Hz, 1H), 7.91 (d, J=5.4 Hz, 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, 5435-54-1, 3-Nitropyridin-4-ol.

Reference:
Patent; ARDEA BIOSCIENCES; US2007/244164; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 944896-42-8, 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 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

[Step a] To a mixed solution of compound 1 (210 mg, 533 mumol) obtained in Reference Example 65, Step b, in dioxane (4.00 mL) and water (500 muL) were added potassium carbonate (170 mg, 1.23 mmol), compound 2 (, 100 mg, 415 mumol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (30 mg, 42.3 mumol), and the mixture was heated in a nitrogen atmosphere under microwave radiation at 150C, and stirred for 1 hr. The reaction solution was allowed to cool to room temperature, 1 M-hydrochloric acid (3.5 mL) was added, and the mixture was extracted with a tetrahydrofuran and ethyl acetate mixed solution (1:1). The aqueous layer was further extracted with a tetrahydrofuran and chloroform mixed solution (1:1), and the organic layers were combined, washed with saturated brine, and concentrated. The residue was subjected to solid phase extraction purification with a cation exchange resin column (Waters, PoraPak, RxnCX), and the obtained solid was suspended and washed in ethyl acetate (2.00 mL) to give compound 3 (70.0 mg, 39.4%).

According to the analysis of related databases, 944896-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1180132-17-5, 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 1180132-17-5 as follows.

Add to the microwave reaction flask7- [2-Chloro-5-fluoropyrimidin-4-yl) -5-fluoro-2,3-dihydro-1H-benzo [d] pyrrole [1,2-a] imidazole (100 mg, 0.33 mmol, Example 11 Preparation),5 – ((4-ethylpiperazin-1-yl) methyl) pyridin-2-amine(7 mg, 0.33 mmol, prepared in second step), sodium tert-butoxide (64 mg, 0.66 mmol), Pd2 (dba) 3 (30 mg, 0.033 mmol)XantPhos (38 mg, 0.066 mmol) and anhydrous 1,4-dioxane (5 mL).The mixture was microwave reacted at 150 C for 1 hour.Cooled to room temperature, extracted with water (10 mL), and ethyl acetate (40 mL x 3).The organic phases were combined, washed with saturated sodium chloride solution (40 mL x 2), dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH = 10: 1)The resulting residue was purified to give the title compound (15 mg, yellow solid)Yield 9.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1180132-17-5, its application will become more common.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem