Category: pyridine-derivatives

Related Products of 3796-24-5, Adding some certain compound to certain chemical reactions, such as: 3796-24-5, name is 4-(Trifluoromethyl)pyridine,molecular formula is C6H4F3N, 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 3796-24-5.

Reagents and conditions: (i) mCPBA, EtOAc; (ii) POCl3; (iii) PdPPh3) 2C12, Ba(OH)2, DME-H2O, 110 0C; (iv) 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine, Pd(OAc)2, Xantphos, K2CO3, dioxane, 120 0C.[0054] Scheme III above shows a general synthetic route that is used for preparing the compounds III-5. Compounds of formula III-5 can be prepared from intermediate III-l. The formation of chloropyridine derivative III-2 is achieved by treating the corresponding pyridine III-l with m-CPBA in EtOAc followed by conversion of the corresponding N-oxide to the chloropyridine by treating it with POCl3. Intermediate III-2 is then reacted with the corresponding boronic acid derivative to yield compound III- 3 using Suzuki coupling conditions well known for those skilled in the art. This reaction is amenable to a variety of boronic acid derivatives. The pyridine III-3 is then converted in a chloropyridine derivative III-4 using the same two step procedures as used in step 1, m-CPBA oxidation followed by POCl3 treatment. Intermediate III-4 is then treated with 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine in the presence of Pd as a catalyst to yield the final compound III-5.

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. 3796-24-5, 4-(Trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); 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.89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6INO

Preparation 94 To a suspension of 3-iodo-4-methoxypyridine (0.62g), 3-nitrophenylboronic acid (0.57g) and tetrakis(triphenylphosphine)palladium(0) (152mg) in dimetoxyethane (10ml) was added aqueous sodium carbonate (2M, 3.43ml) and the mixture was stirred at 60C for 6 hours. The mixture was diluted with ethyl acetate and washed with aqueous sodium hydroxide (1N) and brine. The separated organic layer was dried over magnesium sulfate and evaporated. The residue was purified with silica gel (25g) column chromatography and eluted with 40-80% ethyl acetate in n-hexane to give 3-(4-methoxypyridin-3-yl)nitrobenzene (84mg). APCI-mass;m/z231(M+H+) 1H-NMR(DMSO-d6): delta;3.90(3H,s), 7.24(1H,d,J=5.8Hz), 7.75(1H,t,J=8.0Hz), 8.00 (1H,d,J=8.0Hz), 8.24(1H,dt,J=8.2Hz,1.1Hz), 8.35(1H,t,J=1.0Hz), 8.48(1H,s), 8.53(1H, d,J=7.6Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89640-55-1, 3-Iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1264820; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 956010-87-0, 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 956010-87-0 as follows.

To compound 12 (100 mg, 0.53 mmol) and morpholine (93 mg, 1.07 mmol) was added a 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was extracted with ethyl acetate, neutralized with 4N HCl solution and again extracted. The combined organic layers were dried over sodium sulfate, and the solvent was evaporated to yield 117mg (95 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 3.63-3.75 (m, 6H), 4.07-4.15 (m, 2H), 7.32 (dd, J=8.1, 4.5Hz, 1H), 8.42 (dd, J=8.1, 1.5Hz, 1H), 8.60 (dd, J=4.5, 1.5Hz, 1H), 14.15 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 42.3, 46.9, 66.1, 66.4, 114.8, 118.2, 131.1, 138.1, 149.5, 151.6, 161.0. HRMS m/z calcd for C11H12N4O2: 232.0960; found: 232.0962.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, 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.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%).

According to the analysis of related databases, 915006-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65169-42-8 , The common heterocyclic compound, 65169-42-8, name is Methyl 6-chloro-5-methylnicotinate, molecular formula is C8H8ClNO2, 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.

Preparation 3; 5-Formyl-3-methyl-2-pyridinecarbonitrile (Used to prepare Example 32) (a) (6-Chloro-5-methyl-3-pyridinyl)methanolTo a solution of methyl 6-chloro-5-methyl-3-pyridinecarboxylate (84 mg, 0.453 mmol) in DCM (2 ml), DIBAL-H (1.5 M solution in toluene, 0.905 ml, 1.358 mmol) was added dropwise under N2 at -78 C. The reaction mixture was allowed to attain rt and stirred overnight. After 18 h, TLC showed no starting material. The reaction was quenched by addition of sodium-potassium tartrate saturated solution, extracted with DCM, dried, filtered, and concentrated to afford (6-chloro-5-methyl-3-pyridinyl)methanol (63 mg, 0.400 mmol, 88% yield) pure enough to be used in the next step.1H-NMR (delta ppm, CDCl3): 8.17 (s, 1H), 7.60 (s, 1H), 4.69 (s, 2H), 2.37 (s, 3H).

The synthetic route of 65169-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alemparte-Gallardo, Carlos; Barfoot, Christopher; Barros-Aguirre, David; Cacho-Izquierdo, Monica; Fiandor Roman, Jose Maria; Hennessy, Alan Joseph; Pearson, Neil David; Remuinan-Blanco, Modesto Jesus; US2009/306089; (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. 69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, 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: 2,4,6-Trichloronicotinic acid

EXAMPLE 3D /erf-butyl 2-(2,4,6-trichloronicotinamido)ethylcarbamate A solution of the product of EXAMPLE 3C (6.0 g, 26.5 mmol) in dichloromethane (150 mL) was treated at 0C with 2 drops of N-dimethy lformamide. Oxalyl chloride (6.73 g, 53 mmol) was added dropwise over 30 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. A solution of the acid chloride (4.5 g, 18.4 mmol) in 60 mL of dry dichloromethane was added dropwise over 1 hour to a solution of tert-butyl 2-aminoethylcarbamate (5.9 g, 36.8 mmol) and triethylamine (3.7 g, 36.8 mmol) in 40 mL of dry dichloromethane at 0C and stirring was continued for 2 hours. The mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 390 (M+Na+).

With the rapid development of chemical substances, we look forward to future research findings about 69422-72-6.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188637-63-0, (6-Bromopyridin-2-yl)methanamine, 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, HPLC of Formula: C6H7BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H7BrN2

General procedure: The reaction substrate (0.3 mmol) was added to the reaction vessel.Benzyl alcohol (2mL) and tert-butyl nitrite (1.5equiv),Pumping the reaction vessel – nitrogen-filled operation for 3 consecutive times, reacting at room temperature, after the reaction is over,Diluted with ethyl acetate, concentrated under reduced pressure, and the concentrate was separated by column chromatography(wherein silica gel is 300-400 mesh silica gel), the ratio of petroleum ether to ethyl acetate isThe 4:1 mixture was used as an eluent, and the eluate was collected, and the solution was spun off to obtain a product.

The synthetic route of 188637-63-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou University; Liu Miaochang; Zhang Xue; An Cui; Cai Yueming; Yang Yefei; Zhou Yunbing; Wu Huayue; (18 pag.)CN109503575; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22282-99-1, 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.22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

To a solution of compound 5-5 (26 g, 151.14 mmol, 1 eq) and compound 5-6 (23.40 g, 198.09 mmol, 24 mL, 1.31 eq) in tetrahydrofuran (300 mL) was added LDA (2 M, 39 mL) at -70C under nitrogen atmosphere. The mixture was stirred at -70C for 1 hour prior to the addition of LDA (2 M, 39.00 mL). The reaction was stirred at -70C for another 1 hour. LCMS showed 25% of starting material remained and 54% of desired compound mass was detected. The reaction mixture was quenched with water (50 mL), and extracted with ethyl acetate (100 mLx3). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by reverse phase flash (trifluoroacetic acid condition). Then basified with saturated sodium bicarbonate (10 mL), extracted with ethyl acetate (100 mLx3). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to give compound 5-7 (22 g, 59.63% yield) as yellow oil. 1H NMR (CDCl3, 400 MHz): d 8.45 (d, J = 5.6 Hz, 1H), 7.61 (d, J = 2.0 Hz, 1H), 7.50 (dd, J1 =5.6 Hz, J2 = 2.0 Hz, 1H), 4.20 (q, J = 7.2 Hz, 2H), 3.89 (s, 2H), 1.27 (t, J = 7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 22282-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13296-04-3, 4-(Pyridin-4-yl)aniline, 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, Safety of 4-(Pyridin-4-yl)aniline, blongs to pyridine-derivatives compound. Safety of 4-(Pyridin-4-yl)aniline

EXAMPLE 2 N-Methyl-N’-[4-(4-pyridinyl)phenyl]urea–To 10.52 g. of 4-(4-pyridinyl)benzeneamine suspended in 400 ml. of chloroform was added with stirring 0.76 g. of N,N-dimethyl-4-pyridineamine and 5.5 ml. of methyl isocyanate. The resulting reaction mixture was stirred under reflux for sixteen hours. The reaction mixture was filtered to collect the suspended solid and the filtrate was concentrated in vacuo to yield more solid product plus an oily material. The collected solid was recrystallized from 550 ml. of acetonitrile and dried at 90 C. in vacuo to yield 6.58 g. of N-methyl-N’-[4-(4-pyridinyl)phenyl]urea, m.p. 233-234 C. Another 3.22 g. of this product, m.p. 233-234 C., was obtained by recrystallizing from methanol the above-noted material obtained by concentration of the reaction filtrate.

The synthetic route of 13296-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sterling Drug Inc.; US4376775; (1983); A;,
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. 188637-63-0, name is (6-Bromopyridin-2-yl)methanamine, the common compound, a new synthetic route is introduced below. Formula: C6H7BrN2

To a solution of C-(6-Bromo-pyridin-2-yl)-methylamine (5440 mg, 29.08 MMOL) in dichloromethane (100 mL) at room temperature was added triethylamine (5886 mg, 58.17 MMOL) and acetyl chloride (2511 mg, 31.99 MMOL). The reaction mixture was heated at 40C for 3h and cooled down to room temperature. A solution of sodium hydroxide (1 N) was added and the reaction was stirred for 1 h at room temperature. The layers were separated and the organic phase was concentrated under reduced pressure. The crude mixture was dissolved in EtOH (50 mL) and concentrated hydrochloric acid (10 mL) was added. The mixture was stirred for 30 min and benzene was added followed by sodium hydroxide pellets until pH 10 was reached. The phases were separated and the organic layer was washed with an aqueous solution of ammonium chloride and the volatiles were removed in vacuo. The crude material was purified by column chromatography with a gradient of 0 to 5% METHANOL/DICHLOROMETHANE to give N- (6-Bromo-pyridin-2-ylmethyl)- acetamide as viscous orange oil. MS ES (MH+ 229.1/231. 0).

The synthetic route of 188637-63-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/14566; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem