Tag: M.W:100-200

Electric Literature of 152398-05-5, 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 152398-05-5, name is 3-Aminopyridine-4-methanol. This compound has unique chemical properties. The synthetic route is as follows.

Manganese dioxide (29 gr.; 334 mmoles) was added, in one portion, at room temperature, to a suspension of 3-amino-4-hydroxymethyl pyridine 290 (5.0 gr.; 40.3 mmoles) in 500 ml of chloroform with good stirring. After two days, the solid is filtered through a pad of Celite and washed with chloroform. Removal of the solvent using reduced pressure yielded 4.2 grams (85%) of Compound 291 as a yellow solid.

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 152398-05-5, 3-Aminopyridine-4-methanol.

Reference:
Patent; SCHERING CORPORATION; WO2008/108957; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7598-35-8, Adding some certain compound to certain chemical reactions, such as: 7598-35-8, name is 2-Bromopyridin-4-amine,molecular formula is C5H5BrN2, 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 7598-35-8.

2-Bromo-5-iodopyridin-4-amine (5); [00192] 4-Amino-2-bromopyridine (22.8g, 131 .8mmole) and sodium acetate (20.8g 254mmole) were stirred in acetic acid (82ml_) and a solution of iodine monochloride (1 M in acetic acid, 134ml_, 134 mmole) was added. The mixture was stirred and heated at 75C for 3 hours. Most of the acetic acid was evaporated and the residue was partitioned between water (500ml_) and ethyl acetate (550ml_). The aqueous was again extracted with ethyl acetate (300ml_) The combined extracts were washed twice with 10% sodium carbonate solution (600, 300ml_), with 10% sodium thiosulfate solution (200ml_), with water and with brine, then dried and evaporated. This gave 40.3g of a crude product mix. This was combined with the crude product from a reaction on 7.5g of 4-amino-2- bromopyridine for purification. A large silica column (9cm internal diameter with 28cm bed of silica) was prepared in 5% ethyl acetate in dichloromethane. The crude material was applied in the same solvent. The column was eluted with 5% ethyl acetate in dichloromethane, with 10% ethyl acetate in dichloromethane and with 20% ethyl acetate in dichloromethane to give the desired isomer 5 (20.2g, 38%): 1 H-NMR (CDCI3, 500MHz): delta 4.74 (br s, 2H, NH2), 6.80 (s, 1 H), 8.34 (s, 1 H); and subsequently with 1 :1 ethyl acetate:dichloromethane to give 6 undesired isomer: 2-bromo-3-iodopyridin-4- amine 6 (19.3g, 37%).

According to the analysis of related databases, 7598-35-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); 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.174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, molecular weight is 113.09, as common compound, the synthetic route is as follows.Quality Control of 2-Fluoropyridin-3-ol

A solution comprising 2,3,4,6-Tetra-O- acetyl-a-D-galactopyranosyl bromide 3 (1 .0 g, 2.4 mmol), Ag2C03 (0.74 g, 2.7 mmol), MS- 4A (5 g) and 2-fluoro-pyridin-3-ol 5 (0.33 g, 2.9 mmol) in anhydrous DCM (15 mL ) is stirred overnight, in the dark, at room temperature, under an argon atmosphere. TLC analysis indicated the complete consumption of the starting bromide and the formation of a new nonpolar product. The solution is filtered through a celite, which was rinsed with DCM (3 x 10 mL ). After removing the solvent under reduced pressure, the crude residue is purified directly using silica gel column chromatography, using an increasing gradient of EtOAc in PE. The product afforded is a colorless solid (0.51 g, 51 %). (0101) [0074] TLC: Rf = 0.5 (EtOAc: PE = 1 : 1 ); 1H NMR (600 MHz, Chloroform-d) delta 7.94 (d, J= 4.6 Hz, 1 H, ArH), 7.58 (t, J= 7.8 Hz, 1 H, ArH), 7.13 (dd, J= 7.8, 4.8 Hz, 1 H, ArH), 5.50 (dd, J= 10.5, 7.9 Hz, 1 H), 5.45 (d, J= 3.4 Hz, 1 H), 5.10 (dd, J= 10.5, 3.4 Hz, 1 H), 4.96 (d, J= 7.9 Hz, 1 H), 4.22 (dd, J= 1 1.4, 6.8 Hz, 1 H), 4.15 (dd, J= 1 1 .4, 6.3 Hz, 1 H), 4.01 (td, J = 6.8, 1 .1 Hz, 1 H), 2.19 (s, 3H, OAc), 2.1 1 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.02 (s, 3H, OAc); 13C NMR (151 MHz, CDCI3) delta 170.26 (COquart), 170.13 (COquart), 170.04 (COquart), 169.44 (COquart), 154.75 (d, J= 239.9 Hz), 141 .59 (d, J= 13.4 Hz, ArC), 139.49 (d, J= 25.5 Hz, ArC), 130.22 (d, J = 3.5 Hz, ArC), 121.85 (d, J = 4.3 Hz, ArC), 121.23 (CH), 101.12 (CH), 71.38 (CH), 70.5 (CH), 68.29 (CH), 66.70 (CH), 61.17 (CH2), 21.03 (OAc), 20.63 (OAc), 20.61 (OAc), 20.55 (OAc).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,174669-74-0, 2-Fluoropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; EBERHARD KARLS UNIVERSITAET TUEBINGEN MEDIZINISCHE FAKULTAET; COTTON, Jonathan; KUEHN, Anna; MAURER, Andreas; PICHLER, Bernd; SCHULZE-OSTHOFF, Klaus; FUCHS, Kerstin; KRUEGER, Marcel Andre; ZENDER, Lars; (42 pag.)WO2018/153966; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7295-76-3, 3-Methoxypyridine, 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, 7295-76-3, blongs to pyridine-derivatives compound. COA of Formula: C6H7NO

General procedure: [Li(TMP)Zn(tBu)2] 1 was made according to the literature procedure2 on a 0.4 mmol scale in THF solution. To this solution 3-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. This solution was then transferred to a THF (1 mL) solution of PdCl2(dppf) (29.3 mg, 10 mol %) and 1-bromo-4-chlorobenzene (76.6 mg, 0.4 mmol) to give a heterogeneous red solution. The reaction mixture was then reacted in the microwave at 100C for 10 minutes. The reaction was then quenched with saturated NH4Cl solution (2 mL) and extracted with DCM (3 x 1 mL). The organic fractions were combined and dried by passing through a phase separator cartridge with a hydrophobic frit and the solvent removed under reduced pressure. The residue was purified by column chromatography using a 4 g C18 silica cartridge and eluent Acetonitrile + 0.1 % formic acid:H2O + 0.1 % formic acid (5:95 to 95:5) to give compound 3b as an off white solid 26.5 mg (30% yield) 1H NMR (400 MHz, CDCl3) delta ppm 3.93 (s, 3H) 7.24 (d, J=4.69 Hz, 1 H) 7.39 – 7.46 (m, 2 H) 7.48 – 7.56 (m, 2 H) 8.33 (d, J=4.49 Hz, 1 H) 8.39 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7295-76-3, its application will become more common.

Reference:
Article; Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C.; Tetrahedron Letters; vol. 52; 36; (2011); p. 4590 – 4594;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58483-95-7 , The common heterocyclic compound, 58483-95-7, name is 5-Amino-2-chloropyridine-4-carboxylic acid, molecular formula is C6H5ClN2O2, 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.

6-Chloro-3H-pyrido[3,4-d]pyrimidin-4-one. A solution of 5-amino-2-chloropyridine-4-carboxylic acid (8.1 g, 4.7 mmol) in formamide (100 mL) is stirred at 140° C. for 12 h. Dilution of the cooled mixture with water gives a precipitate of 6-chloro-3H-pyrido[3,4-d]pyrimidin-4-one (7.3 g, 86percent yield). 1 H NMR (DMSO) delta 12.73 (1H, m), 8.90 (1H, d, J=0.7 Hz), 8.23 (1H, s), 7.97 (1H, d, J=0.7 Hz).

The synthetic route of 58483-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US5654307; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13143-47-0, 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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 1-(4-aminophenyl)pyridin-2(1H)-one (3a) (0.90 g, 4.8 mmol), K2CO3 (0.80 g, 5.8 mmol) and DMAP (0.05 g, 0.4 mmol) inTHF (20 mL), solution of 2-nitrobenzoyl chloride (2a) (1.15 g, 6.24 mmol) in THF (5 mL) was addedat room temperature and the mixture was refluxed for 2 h. The reaction mixture was cooled downto room temperature and concentrated under reduced pressure. Then water (100 mL) was addedto the mixture and stirred for 10 min at room temperature. The resulting precipitate was collectedby filtration. The reaction was monitored by TLC with EA.

The chemical industry reduces the impact on the environment during synthesis 13143-47-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Wenzhi; Yuan, Jing; Fu, Xiaoli; Meng, Fancui; Zhang, Shijun; Xu, Weiren; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 21; 4; (2016);,
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. 7584-05-6, name is 3-Methylisonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6N2

Preparation of (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile; [00150] To a solution of 3-methylisonicotinonitrile (10 g, 85 mmol) in DMF (100 mL) was added l,l-dimethoxy-N,N-dimethylmethanamine (18.05 mL, 135 mmol). The mixture was heated to reflux overnight. The mixture was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture, and it was again heated to reflux. After heating the mixture overnight, it was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture. The mixture was heated overnight at reflux. The mixture was cooled to rt and an additional 3.0 mL of 1 , 1 -dimethoxy-N,N- dimethylmethanamine were added. The mixture was again heated to reflux. After heating the mixture overnight, it was cooled to rt. To the mixture was added 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine. The mixture was heated to reflux overnight. The mixture was cooled to rt and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and was loaded onto a BIOTAGE 65 + M cartridge and was purified using a 10-70% EtOAc in hexanes gradient. The expected product, (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile (7.97 g, 46.0 mmol, 54.4 % yield), was isolated as a bright-yellow solid. LC/MS: m/z 174.11 (M+H)+ , 1.690 min (method 1). 1H NMR (500 MHz, chloroform-^) I ppm 1H NMR (500 MHz, chloroform-^ I ppm 8.69 (s, 1 H) 8.14 (d, J= 5.19 Hz, 1 H) 7.23 (d, J= 4.88 Hz, 1 H) 7.15 (d, J= 13.43 Hz, 1 H) 5.21 (d, J= 13.73 Hz, 1 H) 2.95 (s, 6 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, 7584-05-6, 3-Methylisonicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158396; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 717843-48-6, name is 3-Bromo-6-methylpicolinonitrile, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5BrN2

A solution of 2-(tetaut-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methylpicolinonitrile (from step 2) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(t?phenyl-phosphine)palladium (5 mol%) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 1000C and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-70% ethyl acetate in hexane to give 3- methylbenzo[f][l,7]naphthyridin-5-amine as a yellow solid. 1H NMR (methanol d-4): delta 8.85 (d, IH), 8.38 (d, IH), 7.72 (d, IH), 7.53-7.61 (m, 2H), 7.34-7.38 (dd, IH), 2.76 (s, 3H). LRMS [M+H] = 210.1

The synthetic route of 717843-48-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1427-06-1, name is Methyl 6-fluoropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. COA of Formula: C7H6FNO2

General procedure: To a 5 mL vial containing a stir bar, 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (50 mg, 0.19 mmol) and 4-fluorobenzonitrile (26 mg, 0.21 mmol) were added Cs2CO3(96 mg, 0.29 mmol) and 0.55 mL DMSO. The resultant mixture was stirred at 80 Celsius for approximately 15 hours. The mixture was cooled to room temperature and then passed through a syringe filter. The filtrate was subjected to FCC to give the title compound (36 mg, 52%). The title compound was prepared using conditions similar to those described in Example 101 using acetonitrile with 10% DMF as the solvent and 6-fluoronicotinic acid methyl ester. MS (ESI): mass calcd. for C21H19FN4O3, 394.14; m/z found, 395.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.77 (dd, J=2.3, 0.5, 1H), 8.46 (s, 1H), 8.31 (dd, J=8.6, 2.3, 1H), 8.08 (d, J=1.3, 1H), 7.83-7.76 (m, 1H), 7.23 (d, J=8.3, 1H), 7.04 (dd, J=8.6, 0.6, 1H), 4.68 (s, 2H), 3.91 (s, 3H), 3.67-3.55 (m, 1H), 2.23-2.07 (m, 4H), 2.00-1.87 (m, 1H), 1.85-1.75 (m, 1H).

The synthetic route of 1427-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 70298-89-4, 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. 70298-89-4, name is 2,2-Dimethyl-N-pyridin-4-yl-propionamide, molecular formula is C10H14N2O, 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.

N-(Pyridin-4-yl)pivalamide (377 mg, 2.12 mmol) was dissolved in anhydrous tetrahydrofuran under inert atmosphere and cooled to – 78 °C. Within 1 h, a 1.6 M hexane solution of buthyl-lithium (3.3 mL, 5.29 mmol, 2.5eq) was added drop wise. Then the reaction mixture was warmed to 0 °C, stirred for 3 h, and anhydrous dimethylformamide (0.5 mL, 6.35 mmol, 3eq) in anhydrous tetrahydrofuran (3 mL) was added. Subsequently, the solution was warmed to room temperature and stirred for an additional 45 min. The mixture was poured onto a mixture of 6 N HCI (5 mL) and ice (5 g). After stirring for 5 min, the solution was neutralized with K2C03 (3.3 g) and extracted with diethylether. The organic layer was dried over MgS0 and the solvent was removed in vacuo. The residue was purified bycolumnchromatography to get N-(3-formylpyridin-4-yl)pivalamide (258 mg, 59 percent).

According to the analysis of related databases, 70298-89-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem