Category: pyridine-derivatives

Electric Literature of 886365-46-4, 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.886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.

Thionyl chloride (71 mul, 962 mumol) is added to a mixture of 5-chloro-3-methyl-pyridine-2-carboxylic acid (150 mg, 874 mumol), toluene (1 ml) and DMF (20 mul). The mixture is heated to 60 C. for 1 hour. The mixture is concentrated in vacuo and the crude product used directly without further purification.

The chemical industry reduces the impact on the environment during synthesis 886365-46-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); 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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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. Safety of 3-Amino-5,6-dichloropyridine

5-Amino-2,3-dichloropyridine (0.80 g) in dichloromethane (10 ml) was added to boron trifluoride etherate (0.92 ml) at -15 C. under nitrogen. Dichloromethane (15 ml) was added followed by t-butylnitrite (0.71 ml) in dichloromethane (5 ml). After 15 minutes the mixture was allowed to warm to -5 C. over 20 minutes. Hexane was added and the resulting solid was filtered, air-dried and washed with ether and stored at approximately -20 C. overnight. The solid was then heated until gas evolution had ceased and the product kugelrohr distilled to give 2,3-dichloro-5-fluoropyridine (0.104 g).

With the rapid development of chemical substances, we look forward to future research findings about 98121-41-6.

Reference:
Patent; Zeneca Limited; US5922732; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38923-08-9 , The common heterocyclic compound, 38923-08-9, name is Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate, molecular formula is C10H9N3O4, 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 stirred solution of ethyl 6-nitroimidazo[l,2-a]pyridine-2-carboxylate (A34, 7.30 g, 31.73 mmol) in methanol(lOOmL) was added Pd/C(1.6 g, 15.86 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 ballon pressure at room temperature for 4h. after completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get compound ethyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate A35 as a green solid. Yield: 4.50 g(70%) LC-MS(ES) m/z : 205.99[M+H]+.

The synthetic route of 38923-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75115-28-5, Adding some certain compound to certain chemical reactions, such as: 75115-28-5, name is N3-Benzylpyridine-3,4-diamine,molecular formula is C12H13N3, 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 75115-28-5.

General procedure: The vial containing the crude diaminopyridine was equipped with a magnetic stir bar and sealed with a teflon screw cap. Aldehyde (2 mol eqwith respect to the theoretical yield of the first reaction) and then nBuOH was added via syringe to give a diaminopyridine concentration of 0.3 M based on the theoretical yield of the first reaction. The reaction mixture was stirred at 110 C for 18-24 h with needle inserted in septum to expose reaction to air. The mixture was cooled to room temperature, diluted with ethyl acetate, and poured into aqueous saturated NaHCO3. The organic phase was separated and the aqueous phase was extracted twice more into ethyl acetate. The combined organic phases were driedover Na2SO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel, typically using EtOAc, 0 ->10% MeOH.

According to the analysis of related databases, 75115-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chaomin; Chen, Lily; Steinhuebel, Dietrich; Goodman, Andrew; Tetrahedron Letters; vol. 57; 25; (2016); p. 2708 – 2712;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 62135-58-4, Adding some certain compound to certain chemical reactions, such as: 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate,molecular formula is C9H9N3O2, 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 62135-58-4.

Step 2Ethyl 3-(F 1 ,2,4ltriazolo 11 ,5-alpyridin-2-yl)-3 -oxoyrotanoate To a mixture of ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (590 mg, 3.09 mmol) and ethyl acetate (1.81 mL, 18.5 mmol) in THF (6 mL) at -50 C was quickly added lithiumbis(trimethylsilyl)amide (1 M in toluene, 9.26 mL, 9.26 mmol). The mixture was stirred for 30 mm, and then quenched with acetic acid, washed with water, sodium bicarbonate, and brine. Purification by chromatography (silica, 50 – 100% ethyl acetate in hexanes) gave ethyl 3- ([1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-oxopropanoate (350 mg, 49 %) as a clear oil.

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. 62135-58-4, Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BHAGIRATH, Niala; DOMINIQUE, Romyr; KENNEDY-SMITH, Joshua; LUCAS, Matthew C.; PADILLA, Fernando; WO2014/64134; (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.5096-11-7, name is (S)-1-(3-Pyridyl)ethanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.Computed Properties of C7H9NO

EXAMPLE 6 (+)-(R)-1-(3-Pyridyl)ethyl 1-adamantanecarboxylate The method followed that described in Example 1, but using (+)-(R)-1-(3-pyridyl)ethanol [87% ee; prepared by asymmetric reduction of 3-acetylpyridine with (+)-B-chlorodiisopinocampheyl borane, J. Chandrasekharan, P. V. Ranachandran and H. C. Brown, J. Org. Chem., 50, 5446-5448 (1985)] (0.62 g, 5.0 mmol) in THF (20 ml), n-butyllithium (2.5 M; 2.0 ml, 5.0 mmol) in hexane, and 1-adamantanecarbonyl chloride (1.09 g, 5.5 mmol) in THF (5 ml). Chromatography, on elution with ether-petrol-triethylamine 100:50:1, gave the title compound (1.16 g, 81%) as an oil. [alpha]D +29.9 (c 2, MeOH), 87% ee. Recrystallisation of the (-)-(1R)-10-camphorsulfonate salt from ethyl acetate, and reliberation of the free-base, afforded the title compound with 98% ee, [alpha]D +33.7 (c 2, MeOH). IR numax 1728 cm-1; 1 H-NMR (CDCl3) delta1.54 (3H, d, J 6.5 Hz, CHCH3), 1.72 and 1.90 (12H, 2s, adamantyl CH2), 2.03 (3H, s, adamantyl CH), 5.88 (1H, q, J 6.5 Hz, CHCH3), 7.30 (1H, m, Py 5-H), 7.65 (1H, m, Py 4-H), 8.56 (1H, m, Py 6-H), 8.63 (1H, m, Py 2-H); MS m/z 285 (M+). Anal. Calcd: C, 75.76; H, 8.12; N, 4.91. Found: C, 75.30; H, 8.18; N, 4.46%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5096-11-7, (S)-1-(3-Pyridyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; British Technology Group Limited; US5595995; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936841-69-9, 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. 936841-69-9, name is 4-(Trifluoromethyl)picolinonitrile, molecular formula is C7H3F3N2, 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.

A solution of the product from Step B (1.3 g, crude) in a mixed solvent of HC1 (conc.) and dioxane (20 mL, 1:1) was refluxed for 2 hours. The mixture was concentrated to obtain the titleproduct (350 mg, 60% for 2 steps) as a brown solid which was used for the next step without any further purification. MS: MIe 192 (M+1).

According to the analysis of related databases, 936841-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; ZHANG, Guoliang; WO2014/206344; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 178876-83-0, Methyl 6-amino-3-bromopicolinate, 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, 178876-83-0, blongs to pyridine-derivatives compound. SDS of cas: 178876-83-0

A solution of methyl 6-amino-3-bromopyridine-2-carboxylate (20.62 g) (T. R. Kelly and F. Lang, J Org. Chem. 61, 1996, 4623-4633) in chloroform (570 ml) was treated dropwise over 2 hours with bromine (4.62 ml) in chloroform (115 ml) and stirred 16 hours. The solution was washed with excess aqueous sodium bicarbonate, dried and evaporated. Crystallisation from EtOAc/hexane gave the bromopyridine (13.5 g). MS (APCI+) m/z 309,311, 313 (MH+, 70%), 295,297, 299 (100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,178876-83-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4282-47-7, 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 4282-47-7 as follows.

A solution of compound52(0.2 g, 1.03 mmol) in methanol (10 mL) was treated with 10% palladium on carbon (20 mg) and subjected to a hydrogen atmosphere. The mixture was stirred for a further 18 h and then filtered through a pad of Celite. The pad was washed with methanol (50 mL) and the combined filtrates evaporatedin vacuoto give the crude residue which was purified by flash chromatography on silica eluting withCH2Cl2-methanol-aqueous ammonia (95:4.5:0.5) to give amine53(0.15 g, 87%) as a brown solid; mp 89-92 C (lit mp 94-95 C); numax/cm-13333, 3210, 1606, 1586, 1519, 1294, 1181;deltaH(500 MHz, CDCl3) 8.62 (1 H, dt,J1.0, 5.0 Hz), 7.83 (2 H, d,J8.5 Hz), 7.68-7.61 (2 H, m), 7.11 (1 H, m) 6.75 (2 H, d,J8.5 Hz), 3.83 (2 H, br s);deltaC(125 MHz, CDCl3) 157.6, 149.5, 147.5, 136.6, 129.8, 128.1, 121.0, 119.4, 115.2;m/z(ESI) 171 ([M + H]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4282-47-7, its application will become more common.

Reference:
Article; Beinat, Corinne; Reekie, Tristan; Banister, Samuel D.; O’Brien-Brown, James; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Grishin, Anton; Kolesik, Peter; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 277 – 301;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-46-3, 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. 62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, 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.

A mixture of compound 53 (188 mg, 0.37 mmol), 4-bromopicolinamide (75 mg, 0.37 mmol) and 2 M aqueous Na2CO3 (0.6 mL, 1.20 mmol) in DME (3 mL) was degassed in vacuo for 15 min. To the mixture was added Pd(PPh3)4 (48 mg, 0.04 mmol) at room temperature. The mixture was stirred at 100 C under Ar for 8 h. The mixture was poured into water, and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluted with EtOAc in hexane), and crystallized from EtOAc/hexane to give the title compound (62 mg, 33%) as a white solid. mp: 220-222 C. 1H NMR (CDCl3) delta 1.14-1.29 (m, 2H), 1.59-1.76 (m, 2H), 2.20-2.30 (m, 4H), 2.94-3.05 (m, 1H), 3.61-3.75 (m, 1H), 4.60 (d, J = 7.2 Hz, 1H), 5.66 (br s, 1H), 6.34 (d, J = 8.7 Hz, 1H), 7.54 (dd, J = 8.7, 2.3 Hz, 1H), 7.65-7.75 (m, 1H), 7.86-7.94 (m, 3H), 7.99-8.06 (m, 2H), 8.29 (s, 1H), 8.48-8.50 (m, 1H), 8.71 (dd, J = 4.9, 0.8 Hz, 1H). LC/MS m/z 505.1 (M+H). Anal. Calcd for C24H23N4O3SF3: C, 57.13; H, 4.59; N, 11.10. Found: C, 57.04; H, 4.65; N, 10.92.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 62150-46-3, 4-Bromopicolinamide.

Reference:
Article; Tawaraishi, Taisuke; Sakauchi, Nobuki; Hidaka, Kousuke; Yoshikawa, Kyoko; Okui, Toshitake; Kuno, Haruhiko; Chisaki, Ikumi; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3067 – 3072;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem