Category: pyridine-derivatives

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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., name: 3-Iodo-1H-pyrazolo[3,4-b]pyridine

Add 400 g (1.63 mol, 1.0 eq) of 3-iodo-1H-pyrazolo[3,4-b]pyridine, 369 g (1.96 mol, 1.2 eq) of o-fluorobenzyl bromide and 450 g (3.27 mol, 1.5 eq) of K2CO3 dissolved in 4L of DMF into a 5L 4-neck flask and react for 10 h at room temperature. Pour the reaction solution into water after thorough reaction as monitored by TLC, stir it to appear a plenty of grey solid, filter and recrystallize PE: EA=5:1 to obtain 411 g of light yellow solid. The yield is 71.16%. [0025] 11 H NMR (400 MHz, CDCl3) delta (ppm): 8.62 (d, 1H), 7.85 (d, 1H), 7.27 (dd, 1H), 7.11 (dd, 1H); 6.96-7.08 m, 3H), 5.82 (s, 2H).

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, 117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Pharmablock (Nanjing) R&D Co., Ltd.; Li, Jin; Yang, Xiaoyu; Zhu, Jingwei; Yang, Minmin; Wu, Xihan; US2014/309425; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55717-45-8, 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.55717-45-8, name is 6-Bromopyridin-3-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

Compound (II-3) (5.00 g, 28.7 mmol) was dissolved in DMF (30 mL), potassium carbonate (7.94 g, 57.5 mmol),benzyl bromide (4.1 mL, 35 mmol) and TBAI (531 mg, 1.44 mmol) were added under ice-cooling, and the mixture waswarmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydroussodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (n-hexane:ethyl acetate = 97:3 ?80:20) to give compound (M-16) (yield 6.97 g, 92%) as awhite solid

Statistics shows that 55717-45-8 is playing an increasingly important role. we look forward to future research findings about 6-Bromopyridin-3-ol.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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.39856-50-3, name is 5-Bromo-2-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of compound (1) (20.00 g, 98.53 mmol, 1.00 eq) in dimethyl sulfoxide (52 mL), compound (2) (24.00 g, 128.86 mmol, 1.31 eq) and triethylamine (20.00 g, 197.65 mmol, 2.01 eq) were added. The solution was heated to 60 C. and stirred for 18 hours. TLC (petroleum ether:ethyl acetate=3:1) showed the completion of the reaction. The solution was diluted with water (200 mL), stirred for 30 minutes, and then filtered. The filter cake was washed with water and dried under vacuum to obtain a crude product. The crude product was purified by a silica gel column (petroleum ether:ethyl acetate=50:1 to 20:1) to obtain compound (3) (27.00 g, 87.57 mmol, yield: 88.87%). 1H NMR (400 MHz, CDCl3) delta8.18 (d, J=9.03 Hz, 1H), 8.13 (d, J=2.89 Hz, 1H), 7.21 (dd, J=9.10, 2.95 Hz, 1H), 3.69-3.59 (m, 4H), 3.51-3.40 (m, 4H), 1.49 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 39856-50-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 633328-33-3, name is 3-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Example i-2: Preparation of 3-bromo-1H-pyrazolo[4,3-b]pyridine Step 1. Preparation of (3-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)(2-chloro-6- (trifluoromethyl)phenyl)methanone (i-2). To a flask was added 3-bromo-lH-pyrazolo[4,3-b]pyridine (i-2a) (3.2 g, 16.2 mmol), 2- chloro-6-(trifluoromethyl)benzoyl chloride 2 (3.9 g, 16.2 mmol), DMAP (1.97 g, 16.2 mmol) and DCM (60 mL), followed by the addition of TEA (3.26 g, 32.4 mmol) slowly. The reaction mixture was stirred at 40C for 3h. The mixture was diluted with H20, and the organic layer was separated. The aqueous layer was extracted with CH2C12 . The combined organics were washed with H20, brine, dried over Na2S04, and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc, 5/1) to afford 3.0 g (46%) of the title compound. LCMS (ESI) calc’d for Ci4H6BrClF3N30 [M+H]+: 406, found: 406.

With the rapid development of chemical substances, we look forward to future research findings about 633328-33-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); 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. 1065100-83-5, name is (1H-Pyrrolo[2,3-b]pyridin-3-yl)methanol, molecular formula is C8H8N2O, 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. name: (1H-Pyrrolo[2,3-b]pyridin-3-yl)methanol

To a mixture of 1 H-pyrrolo[2,3-b]pyridin-3-yl)methanol (A-3) (1.0 g, 6.75 mmol) in anhydrous THF (50 mL) were added DPPA (3.71 g, 13.5 mmol) and DBU (0.821 g, 5.4 mmol) respectively. It was refluxed under N2 for 6 h, and then concentrated under vacuo. The resulting residue was dissolved in EtOAc (50 mL), washed with brine, dried over sodium sulfate and concentrated under vacuo, to obtain the crude product. The crude product was purified by chromatography on silica gel to afford the title compound (0.587 g). MS (m/z): 174 (M+1 )+.

With the rapid development of chemical substances, we look forward to future research findings about 1065100-83-5.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113770-88-0, Adding some certain compound to certain chemical reactions, such as: 113770-88-0, name is 3-Fluoro-4-cyanopyridine,molecular formula is C6H3FN2, 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 113770-88-0.

Example 15A 1H-Pyrazolo[3,4-c]pyridin-3-amine 3-Fluoro-isonicotinonitrile (0.50 g, 4.10 mmol) was dissolved in ethanol (8 mL) and treated with hydrazine hydrate (0.31 g, 6.1 mmol). After stirring at 70 C. for 16 h, the mixture was cooled to RT and concentrated in vacuo and dried to yield the title compound (0.66 g, 100% of theory). LC-MS (Method 2B): Rt=0.51 min, MS (ESIPos): m/z=135 [M+H]+

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. 113770-88-0, 3-Fluoro-4-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Hassfeld, Jorma; KINZEL, Tom; Koebberling, Johannes; CANCHO GRANDE, Yolanda; BEYER, Kristin; Roehrig, Susanne; Koellnberger, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; US2015/126449; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 71902-33-5 , The common heterocyclic compound, 71902-33-5, name is 3,5-Difluoropyridine, molecular formula is C5H3F2N, 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.

General procedure: An oven-dried reaction vessel (4 or 9 ml screw-cap vial) equipped with a stirring bar was allowed to cool to room temperature under vacuum. Activated 4 A molecular sieves (crushed, 50 mg), [Rh-2 ] (and solid substrates, 1.0 equiv.), were added under air. The vial was then depressurized and pressurized with argon gas three times before the addition of dry THF (1 M) (and liquid substrates, distilled over CaH2, 1.0 equiv.). Following the addition of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.0-4.0 equiv. as indicated), the glass vial was placed in a 150 ml stainless-steel autoclave under an argon atmosphere. The autoclave was pressurized and depressurized with hydrogen gas three times before the indicated pressure was set. The reaction mixture was stirred at 25-40 C for 24 h. After the autoclave was carefully depressurized, trifluoroacetic anhydride (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the crude mixture and stirring was continued for 10 min at room temperature. Alternatively, di-tert-butyl dicarbonate (3.0 equiv.), triethyl amine (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the reaction mixture and stirring was continued for 2 h at room temperature. The crude was then filtered over fritted funnel and the remaining solid was washed with ethyl acetate (2x 5 ml). The combined solution was concentrated under reduced pressure and submitted to column chromatography (pentane/ethyl acetate or pentane/dichloromethane) to obtain the final product. The indicated diastereoselectivities were determined by GC analysis or from the 19F NMR spectrum immediately after the reaction. NMR yield was calculated using hexafluorobenzene (20 mul, 0.173 mmol) as internal standard.

The synthetic route of 71902-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nairoukh, Zackaria; Wollenburg, Marco; Schlepphorst, Christoph; Bergander, Klaus; Glorius, Frank; Nature Chemistry; vol. 11; 3; (2019); p. 264 – 270;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 68963-75-7, 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. 68963-75-7, name is 4,6-Dichloropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

2,4-Dichloro-6-hydroxypyridine (696mg, 4.2mmol), 3-exo-hydroxy-8- azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (965mg, 4.2mmol) and (4,4- Dimethyl-1 ,1-dioxido-1 ,2,5-thiadiazolidin-2-yl)triphenylphosphonium (4.31g, 10.5mmol) in THF (2OmL) were stirred for 16h. Ethyl acetate (5OmL) and water (2OmL) were added and the organic and aqueous layers were separated. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 3-exo-(4,6-dichloropyridin-2- yloxy)-8-azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (1.29g, 3.6mmol, 82percent). M.S. (ESI) m/z: 373,375 [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,68963-75-7, its application will become more common.

Reference:
Patent; N.V. ORGANON; WO2007/63071; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 115170-40-6 ,Some common heterocyclic compound, 115170-40-6, molecular formula is C7H7BrN2, 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) 30g (0.151mol) of 5-bromo-7-azaporphyrin, 60g of activated carbon fiber catalyst, 264g of xylene into the reaction flask, stirring evenly, to obtain a reaction mixture G;b) The reaction mixture G at 100 C, oxygen flow 200mL/min, reaction 8h, chromatographic monitoring of the disappearance of raw materials;c) Filtration, filter out activated carbon fiber catalyst, obtain organic layer H, recover solvent, get 5-bromo-7-azaindole crude product, recrystallize from methanol to obtain product 25.37g, yield 85.43%, content ?99% .

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. 115170-40-6, 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhonggang Group Anshan Heat Energy Institute Co., Ltd.; Wang Haiyang; Wang Shoukai; Xu Zhe; Zhao Wei; Jiang Hui; Jin Dan; Xu Haoran; (7 pag.)CN107987076; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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.

General procedure: To a 50 mL two-necked flask equipped with magnetic stirrer and condenser was added 2-bromopyridine (1.0 eq), Pd(PPh3)4 (5 mol%), K2CO3 solution (2.0 eq) and toluene under N2 at room temperture. After reacted for 15 min, a solution of the boronic acid (1.2 eq) in EtOH was then added. The reaction mixture was then heated to 95 C and reacted for 4 h. After cooling to room temperature, to the reaction mixture aqueous NH4Cl was added and extracted three times with EtOAc. The organic extracts were then combined, washed with brine, dried with MgSO4 and then concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography(Petroleum ether/EtOAc) to give compounds 1 and 5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Article; Duan, Yingchao; Qin, Wenping; Suo, Fengzhi; Zhai, Xiaoyu; Guan, Yuanyuan; Wang, Xiaojuan; Zheng, Yichao; Liu, Hongmin; Bioorganic and Medicinal Chemistry; vol. 26; 23-24; (2018); p. 6000 – 6014;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem