Category: pyridine-derivatives

Electric Literature of 58481-11-1, 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. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, 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.

1. Synthesis of methyl 2-(thiazol-2-ylamino)isonicotinate A suspension of methyl 2-chloroisonicotinate (15.0 g, 87.42 mmol), 2-aminothiazole (10.50 g, 104.9 mmol), sodium carbonate (12.97 g, 122.4 mmol, 1.4 eq) and XANTPHOS (0.607 g, 1.049 mmol, 0.012 eq) in toluene (300 mL, bubbled with argon for 5 minutes) was bubbled again with argon for 5 additional minutes. Tris(dibenzylideneacetone)dipalladium (0) (0.320 g, 0.349 mmol, 0.004 eq) was then added to the suspension which was heated at 100° C. for 5 days. The mixture was cooled down to RT and filtered. The resulting solid was suspended in water and stirred for 1 hour. After filtration, the resulting solid was dried under vacuum overnight and afforded the title material (14.17, 69percent) as a solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 3.90 (3H, s), 7.07 (1H, d, J=3.54), 7.32 (1H, dd, J=5.31, 1.26 Hz), 7.43 (1H, d, J=3.79 Hz), 7.61 (1H, s), 8.48 (1H, d, J=4.55 Hz), 11.56 (1H, s). LC/MS (M+H)+: 236. HPLC ret. time (Condition A): 1.182 min.

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; US2010/48581; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1072-97-5, 5-Bromopyridin-2-amine, 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, 1072-97-5, blongs to pyridine-derivatives compound. Product Details of 1072-97-5

General procedure: To a solution of 2a, 2c or 2h (3 mmol, 0.5 g) in ethylene glycol (5 mL) was added successively the boronic acid (4.5 or 9.0 mmol, 1.5 or 3 equiv), Pd(PPh3)4 (1mol%), and a solution of K3PO4 (6 mmol, 2 equiv) inwater (2 mL). The reaction mixture was heated at 80C for 16 h and was then hydrolyzed with a 1 M solution of sodium hydroxide (20 mL). The aqueous phase was extracted with ethylacetate (3 x 30 mL) and the combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/EtOAc (60/40) as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-97-5, its application will become more common.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1174229-72-1 ,Some common heterocyclic compound, 1174229-72-1, molecular formula is C9H12N2O2, 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 a solution of ethyl 2-(6-aminopyridin-3-yl)acetate (1.7 g, 9.4 mmol) in t-BuOH (25was added TEA (1.1 g, 11.3 mmol) and (Boc)20 (2.5 g, 11.3 mol). The mixture was stirred at 50 C for 3h and then the reaction mixture was concentrated and the residue was purified by column chromatography (silica gel, PE : EtOAc = 10 : 1) to give ethyl 2-(6-((tert-butoxy- carbonyl)amino)pyridin-3-yl)acetate (1.9 g, 73%) as a white solid.

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. 1174229-72-1, Ethyl 2-(6-aminopyridin-3-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); 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.128071-75-0, name is 2-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.COA of Formula: C6H4BrNO

General procedure: In a 20 mL glass tube equipped with septa, the aldehyde, dry Na2SO4 (2.81 equiv) and triethylamine (2 equiv) were suspended in dry THF. Then, the hydroxylamine hydrochloride (2 equiv) was added. The mixture was stirred for 30 s, and then exposed to MWI (250 W) at 80 C during the time indicated for each compound. When the reaction was(TLC analysis), the reaction mixture was diluted with water, extracted with CH2Cl2, driedanhydrous sodium sulphate, filtered and the solvent was evaporated. The resultant solid was purified by column chromatography to give pure compounds.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,128071-75-0, 2-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Samadi, Abdelouahid; Soriano, Elena; Revuelta, Julia; Valderas, Carolina; Chioua, Mourad; Garrido, Ignacio; Bartolome, Begona; Tomassolli, Isabelle; Ismaili, Lhassane; Gonzalez-Lafuente, Laura; Villarroya, Mercedes; Garcia, Antonio G.; Oset-Gasque, Maria J.; Marco-Contelles, Jose; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 951 – 960;,
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. 20265-38-7, name is 2-Methoxypyridin-3-amine. A new synthetic method of this compound is introduced below., Product Details of 20265-38-7

(2) A solution of 2-methoxypyridin-3-amine (39.4 g) in N,N-dimethylformamide (200 mL) was cooled to -30 C., and a solution of N-bromosuccinimide (62.1 g) in N,N-dimethylformamide (100 mL) was added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with chloroform. The organic layer was sequentially washed with a saturated sodium sulfite solution, water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1?4:1) to give 6-bromo-2-methoxypyridin-3-amine as a yellow powder (51.9 g, 80%). 1H NMR (300 MHz, CDCl3) delta ppm 3.64-3.84 (m, 2H), 3.98 (s, 3H), 6.78 (dd, J=7.9, 1.0 Hz, 1H), 6.87 (d, J=7.9 Hz, 1H). MS(+): 203 [M+H]+.

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, 20265-38-7, 2-Methoxypyridin-3-amine.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); 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 918511-92-9, name is 5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C12H9N3

To 3-dibenzylammo-2,6-difluoro-benzaldehyde (53, 0.76 g, 2.3 mmol) in methanol (50 mL) were added 5-pyridin-3-yl-lH-pyrrolo[2,3-b]pyridme (89, 0.40 g, 2.1 mmol, prepared as described in Example 17) and potassium hydroxide (0.50 g, 8.9 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% methanol in methylene chloride to provide the compound (54, 0.60 g, 50%). MS(ESI)

With the rapid development of chemical substances, we look forward to future research findings about 918511-92-9.

Reference:
Patent; PLEXXIKON, INC.; WO2007/2325; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1037223-35-0, 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.1037223-35-0, name is 2-Bromo-6-isopropylpyridine, molecular formula is C8H10BrN, molecular weight is 200.08, as common compound, the synthetic route is as follows.

Compd. 1B (5. 0g, 9. 50mmol), 2-bromo-6-Isopropylcyclohexanecarboxylic polypyridine (3. 0g, 19. 0mmol), sodium carbonate (7. 5g, 19. 0mmol) of dimethyl ether (100 ml)/ water solution (20 ml), tetrakis (triphenylphosphine) palladium (1. 0g, 0. 95mmol) in addition to 10 C, reflux in 12 hours. Ice water (100 ml) is added, the extracted with ethyl acetate (100 ml × 3 times) the reaction liquid. After cleaning the saturated solution, dried with sodium sulfate, filtration, concentrating, column chromatography (ethyl acetate/aminopentanenitrile = 10/1) by purification, yellow oilies compd. 2A is obtained. Yield 4. 0g yield at 83%.

Statistics shows that 1037223-35-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-6-isopropylpyridine.

Reference:
Patent; JAPAN POLYPROPYLENE CORP; JAPAN POLYETHYLENE CORP; KOBAYASHI, MINORU; UCHINO, HIDEFUMI; (40 pag.)JP2015/155397; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 93683-65-9, 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 93683-65-9, name is 6-Chloro-3-nitropicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Generalprocedure. A solution of 6-chloro-2-cyano-3-nitropyridine (1 equiv) in toluene or dioxane/water (see compound description) was degassed with argon and subsequently, the corresponding aryl boronic acid (1.2equiv), Pd(PPh3)4 (0.02 equiv) and K2CO3 (2 equiv) were added. The mixture was degassed a second time, filled with argon and stirred at 95 C overnight. After completion of the reaction as monitored by TLC,the volatiles were evaporated to dryness and the crude residue was diluted with EtOAc (20 mL) and washed with water (2×20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated invacuo. The resulting residue was purified by silica gel flash chromatography, yielding the corresponding 6-aryl-3-nitropyridine-2-carbonitrile. The following compounds were made according to this procedure.

According to the analysis of related databases, 93683-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; De Jonghe, Steven; Einav, Shirit; Froeyen, Mathy; Herdewijn, Piet; Martinez-Gualda, Belen; Pu, Szu-Yuan; Bioorganic and medicinal chemistry; vol. 28; 1; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13362-28-2 ,Some common heterocyclic compound, 13362-28-2, 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.

To a mixture of 6-benzyloxy-1-[(E)-2-(5-benzyloxy-4-methoxy-2-methyl-phenyl)vinyl]-7-methoxy-1,2,3,4-tetrahydroisoquinoline [50 mg (0.097 mmol)], 2-aminopyridine-4-carboxylic acid [13.8 mg (0.1 mmol)], DIEA [50 ul (0.3 mmol)] & 1 mL of DMF was added HATU [47.5 mg (0.125 mmol)]. The reaction was stirred at rt for 1 h and then diluted with 20 mL of EtOAc and washed 2* with sat NaCl. The EtOAc layer was dried (Na2SO4) and the solvent removed. Yield=28 mg (46%) via prep chrom. MS (m/z): 642 [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,13362-28-2, its application will become more common.

Reference:
Patent; Prosetta Antiviral, Inc.; ATUEGBU, Andy; SOLAS, Dennis; HURT, Clarence R.; KITAYGORODSKYY, Anatoliy; (141 pag.)US2016/168100; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-49-6 , The common heterocyclic compound, 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, molecular formula is C10H16N4, 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.

Under N2 atmosphere, to a solution of 2′-chloro-2,3,5,6-tetrahydro-8’H-spiro[pyran- 4,9′-pyrazino[r,2′: l,5]pyrrolo[2,3-d]pyrimidine] (32, 50 mg, 0.18 mmol) and 5-(4- methylpiperazin-l-yl)pyridin-2-amine (52 mg, 0.27 mmol) in dioxane (4 mL) was added CS2CO3 (170 mg, 0.52 mmol), Pd(OAc)2 (8 mg, 0.04 mmol) and X-Phos (12 mg, 0.03 mmol). After stirring at 100 C for 12 h, the mixture was directly concentrated in vacuo. The resulting residue was purified by prep TLC to provide N-(5-(4-methylpiperazin-l-yl)pyridin-2-yl)- 2,3,5,6 etrahydro-8H-spiro[pyran-4,9′-pyrazino[l 2^ 1,5]pyiTolo[2,3-d]pyriiTddin]-2′-amine (COMPOUND 10, 20 mg, 0.05 mmol). MS (ESI+): m/z 433 [M + H]+; NMR (300 MHz, MeOD): delta 8.90 (s, 1H), 8.53 (s, 1H), 8.09 (d, J = 9.0 Hz, 1H), 8.03 (d, J = 3.0 Hz, 1H), 7.70 (d, J= 7.2 Hz, 1H), 7.09 (s, 1H), 4.24 (d, J= 1.7 Hz, 2H), 4.01 (dd, J= 12.3, 4.8 Hz, 2H), 3.77 (t, J = 11.8 Hz, 2H), 3.56 – 3.33 (m, 8H), 3.28 – 3.17 (m, 2H), 2.95 (s, 3H), 1.82 (d, J = 13.6 Hz, 2H).

The synthetic route of 571189-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem