Pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 19337-97-4

(2E)-3-(pyridin-3-yl)prop-2-enoic acid (698 mg, 4.68 mmol) was dissolved in DMF (24 mL) and treated with DIPEA (2 mL, 11.7 mmol) and HATU (1.80 g, 4.68 mmol). After 5 minutes, tert-butyl 4-(4-aminobutyl)piperidine-l -carboxylate (1.00 g, 3.90 mmol) was added as a solution in DMF (8 mL). The reaction was stirred at room temperature overnight. The reaction solvent was removed in vacuo, and the residue redissolved in EtOAc then washed once with water, twice with saturated NaHCC , and once with brine. The organic layer was dried over Na2S04 and concentrated. The crude product was purified by silica gel chromatography (EtOAc/hexanes) to provide the title compound (1.16 g, 3.00 mmol, 77%). LCMS: tR = 1.22 min; m/z = 388.3 [M+H]+. lH NMR (400 MHz, Chloroform-d) delta 8.78 – 8.71 (m, 1H), 8.57 (dd, J = 4.8, 1.6 Hz, 1H), 7.83 – 7.75 (m, 1H), 7.62 (d, J = 15.7 Hz, 1H), 7.35 – 7.29 (m, 1H), 6.45 (d, J = 15.7 Hz, 1H), 5.68 (t, 1H), 4.18 – 3.90 (m, 2H), 3.40 (td, J = 7.2, 5.9 Hz, 2H), 2.76 – 2.55 (m, 2H), 1.70 – 1.51 (m, 4H), 1.45 (s, 9H), 1.43 – 1.31 (m, 3H), 1.31 – 1.20 (m, 2H), 1.07 (qd, J = 12.5, 4.4 Hz, 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, 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; SEATTLE GENETICS, INC.; NEUMANN, Christopher Scott; OLIVAS, Kathleen; (446 pag.)WO2018/75600; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73583-37-6, 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. 73583-37-6, name is 4-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, 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-(2-chloropyridin-4-yl)phenyl)carbamateTo a mixture of (4-boc-aminophenyl)boronic acid (200mg, 0.84mmol) and 2-chloro-4- bromopyridine (162mg, 0.84mmol) in 10ml of 1,4-dioxane, was added PdCl2(PPh3)2 (10mg, 0.014mmol) and 1M Na2CO3 aqueous solution (0.5ml, 1.0mmol). The mixture was heated at 70 C under N2 for 2 hours, cooled to room temperature and poured into 100ml of water. The brown precipitates were filtered, washed with water and dried to give tert-butyl (4-(2- chloropyridin-4-yl)phenyl)carbamate as the crude product.

According to the analysis of related databases, 73583-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; GUO, Xialing; ZHU, Zhen; WO2015/69287; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 94805-51-3, name is 2-Oxo-1,2-dihydropyridine-4-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4N2O

2-Hydroxy-4-cyano-pyridine (240 mg, 2 mmol, 1 equiv.) was dissolved in DMF (6 ml), K2CO3 (415 mg, 3 mmol, 1.5 equiv.) and NaI (60 mg, 0.4 mmol, 0.2 equiv.) were added and the mixture was stirred at r.t. for 10 min. 5-Chloro-2-(chloromethyI)-1,3- benzothiazole (436 mg, 2 mmol, 1 equiv.) was added and the reaction mixture was stirred at 600C for 3 h and at r.t. overnight. By addition of H2O, brown solid precipitated, which was filtered, rinsed with H2O, dried and re-crystallised from CH3CN. Yield 280 mg (46%), mp 224-227C, HPLC-MS (method 1): m/z 302 [M+H]+, Rt = 3.80 min. By 13C-NMR analysis it was identified to be the N-alkylated derivative (Scheme 24). The DMF-H2O mother liquors were evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica, eluted with EtOAc/hexane (10%-100% gradient) to give 45 mg (7.5% yield) of a brown solid, HPLC-MS (method 1): m/z 302 [M+H]+, Rt = 4.86 min. By 13C-NMR analysis, it was identified to be the desired O-alkylated derivative (Scheme 24).

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, 94805-51-3, 2-Oxo-1,2-dihydropyridine-4-carbonitrile.

Reference:
Patent; PROLYSIS LTD; WO2007/107758; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137178-88-2, Adding some certain compound to certain chemical reactions, such as: 137178-88-2, name is 5-Bromopyridine-2-carbonyl chloride,molecular formula is C6H3BrClNO, 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 137178-88-2.

To a solution of 5-bromo-pyridine-2-carboxylic acid methyl ester [(L.] [OEQ.)] (see Synth. Commun., [1997,] [27,] 515) in THF : MeOH (2: 1; 0.2M) was added aqueous LiOH (1M ; 3. [0EQ.).] The mixture was stirred for 12h, concentrated and dried under vacuum. The residue was diluted in CH2CI2 (0.2M), oxalyl chloride [(8.] [OEQ.)] was added and the mixture was stirred for 3h, concentrated, dried under vacuum and diluted in [CH2C12] (0.2M). Cyclopropylamine [(LOEQ.)] was added and the mixture was stirred for 2h, poured in saturated aqueous [NAHC03] and extracted with EtOAc (2x). The combined organic extracts were washed with brine, dried over [NA2S04,] filtered and concentrated. Flash chromatography (CH2Cl2 : EtOAc; 9: 1) afforded the title compound as a yellow 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. 137178-88-2, 5-Bromopyridine-2-carbonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK FROSST CANADA & CO.; DESCHENES, Denis; DUBE, Daniel; DUBE, Laurence; GALLANT, Michel; GIRARD, Yves; LACOMBE, Patrick; MACDONALD, Dwight; WO2004/814; (2003); 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Methylpyridin-2(1H)-one

EXAMPLE 1 5-Methyl-1-phenyl-2-(1H)-pyridone SPC3 A finely pulverized mixture containing 21.8g. of 5-methyl-2-(1H)-pyridone (J.V. Scudi, et al. U.S. Pat. No. 2,947,755), 30.4g. of anhydrous potassium carbonate, 0.25g. of zinc precipitated copper powder and 40 ml. of iodobenzene is stirred mechanically and refluxed for 18 hours. The mixture is cooled and treated with 150 ml. of benzene, filtered and the filtrate is decolorized with charcoal. The decolorized benzene filtrate is then evaporated to an oil which on trituration with petroleum ether and cooling gives 31.9g. (85%) of the product as a brown solid, m.p. 90-104. It is crystallized from hot water to yield a white solid melting at 102-psi.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; Affiliated Medical Research, Inc.; US3974281; (1976); A;,
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. 78607-36-0, name is 2-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-3-iodopyridine

Preparation of amine building block A46 tert-Butyl 2- (pyridin-4-ylmethyl) -5, 6-dihydroimidazo [1,2- a]pyrazine-7 (8H) -carboxylateProcedure for step- 1 : To a THF solution (40 ml) of Diisopropyl amine (4.46 ml, 1.5 eqv) was added BuLi ( 1.88 M, 1.5 eqv) at -15C and the resulting reaction mixture was allowed to stir at same temperature for 20 minutes. It was then cooled to -78C and 2-chloro-3-iodopyridine (5g, 20.92 mmol) in THF (10 ml) was added dropwise at the same temperature and allowed to stir for 1 hr at -780C. Reaction was quenched with water ( 10 ml), stirred at ambient temperature for 15 minutes and extracted with ethyl acetate. Organic layer was washed successively with brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product which was immediately used in the next step without any further purification. Yield : 80% (Crude)

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, 78607-36-0, 2-Chloro-3-iodopyridine.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 94952-46-2, 1-(5-Chloropyridin-2-yl)ethanone, 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, 94952-46-2, blongs to pyridine-derivatives compound. Recommanded Product: 1-(5-Chloropyridin-2-yl)ethanone

Reference Production Example 3. In 50 mL of methanol, 243 mg of sodium borohydride was suspended and 1.00 g of 2-acetyl-5-chloropyridine was added thereto at room temperature. After stirring at the same temperature for 2 hours, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was dissolved in 50 mL of tetrahydrofuran. To the solution were added dropwise 0.5 mL of methanesulfonyl chloride and 0.9 mL of triethylamine at room temperature. After stirring at the same temperature for 2 hours, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was dissolved in 50 mL of N, N-dimethylformamide . To the solution was added 1.12 g of lithium bromide at room temperature. After stirring at the same temperature for 6 hours, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was subjected to column chromatography to obtain 368 mg of 2- ( 1-bromoethyl) -5-chloropyridine .1H-NMR (CDCl3, TMS) : delta (ppm) 8.25 (IH, s), 7.66 (IH, d) , 7.42 (IH, d) , 5.12 (IH, q) , 1,87 (3H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94952-46-2, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/25397; (2009); 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. 1737-93-5, name is 3,5-Dichloro-2,4,6-trifluoropyridine, molecular formula is C5Cl2F3N, 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 3,5-Dichloro-2,4,6-trifluoropyridine

S2.The above solution containing dichlorotrifluoropyridine was cooled to 10 C,And slowly dropping 30wt% aqueous ammonia at 10 C, the reaction was detected by TLC, to be dichloro-trifluoro pyridine reaction was complete,The reaction was stopped and a white solid was isolated as the desired drug intermediate (95.3% yield).

With the rapid development of chemical substances, we look forward to future research findings about 1737-93-5.

Reference:
Patent; Chongqing Huage Biochemical Co., Ltd.; He Xiaoqiang; Chen Zhizhong; Zhang Chunhua; Gu Fuhai; Wu Chengli; Yang Xinyao; (8 pag.)CN107311924; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55589-47-4, 3-Methylpicolinaldehyde, 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: 3-Methylpicolinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 3-Methylpicolinaldehyde

(7-(4-Methylpiperazin-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl)methanamine (50 mg, 0.2 mmol) was dissolved in 2 mL of DCE (1,2-Di Chloroethane) 3-methyl-2-pyridinecarboxaldehyde (0.2 mmol, 24 mg) and NaBH(OAc)3 (64 mg, 0.3 mmol) were added and the mixture was stirred at room temperature for 2 h. Diluted with DCM and washed with saturated sodium bicarbonate and saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated by filtration, and the residue was purified by column chromatography to give the title compound as a pale yellow gum (46percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55589-47-4, 3-Methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Cao Bin; (103 pag.)CN103570683; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1264193-11-4 ,Some common heterocyclic compound, 1264193-11-4, molecular formula is C7H5BrN2, 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: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

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. 1264193-11-4, 6-Bromopyrazolo[1,5-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem