Category: pyridine-derivatives

Application of 4434-13-3, 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 4434-13-3 as follows.

To a mixture of 5-methylpicolinic acid (13.7 g) and thionyl chloride (150 mL) was added sodium bromide (20.6 g) by small portions, and the mixture was heated under reflux under a nitrogen atmosphere for 1 hr. DMF (2 mL) was added and the mixture was further heated under reflux under a nitrogen atmosphere for 16 hr. An operation to add toluene (100 mL) to the reaction mixture and evaporate the solvent under reduced pressure was repeated twice, and toluene (100 mL) was added to the obtained residue. To a mixture thereof were added DIPEA (25.8 g) and methanol (20 mL) under a nitrogen atmosphere at 0C, and the mixture was further stirred at 20C for 2 hr. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.40 g). 1H NMR (400 MHz, CDCl3) delta2.43 (3H, s), 3.99 (3H, s), 8.10 (1H, s), 8.54 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4434-13-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, Adding some certain compound to certain chemical reactions, such as: 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine,molecular formula is C6H7ClN2, 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 66909-38-4.

2-Chloro-4-methyl-5-nitropyridine (lg, 5.8 mmol) was dissolved in EtOH (60 mL). AcOH (4 mL) and Fe (5 eq. ) were added and the mixture was refluxed at 80C overnight. The mixture was filtered through celite and reduced under vacuum to afford the crude 5-amino-2-chloro-4-methylpyridine which was used in the next step with no further purification. The amine was dissolved in cone. HC1 (6 mL), transferred to a 3-neck round bottom flask, and cooled to-5 C. A solution of NaNO2/H2O (440 mgs/5 mL) was slowly added and the mixture was allowed to stir for 10 mins. To a second, separate 3-neck round bottom flask was added H20 (12 mL) and cooled to-5 C. Thionyl chloride (4.5 eq. ) was then added dropwise. After complete addition the mixture was allowed to warm to room temp. Whereupon CuCl (. 05 eq. ) was added and the mixture was then cooled back down to -5C. The first reaction mixture, containing the amine precursor, was slowly added to the second reaction mixture. A froth formed and was filtered off to afford 6-chloro-4-methyl-pyridine-3-sulfonyl chloride which was used in the next step with no further purification. The title compound was synthesized from 2- [2- (R, S)-3-oxo-1, 2,3, 4-tetrahydro-quinoxalin-2-yl]-N- (pyrid- 4-yl) ethyl acetamide and 6-chloro-4-methyl-pyridine-3-sulfonyl chloride using Method G. MS ni/z (M+H) 501.4 ; HPLC (CH3CN-H2O-0.1% TFA): Rt= 2.05 min.

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 114042-02-3, 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. 114042-02-3, name is 5-Bromo-3-methyl-2-nitropyridine, molecular formula is C6H5BrN2O2, 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) Add DMA and DMF to the reaction kettle,The molar ratio of DMA to DMF is 2:3.Stir and mix well,Thereafter, 2-nitro-3-methyl-5-bromopyridine is added thereto.Heat, keep the temperature at 160 C,Carry out a reflux reaction,After the reaction is completed,Distilling the solvent under reduced pressure,Add absolute ethanol,After mixing evenly, suction filtration, washing,Drying2-nitro-3-dimethylamine vinyl-5-bromopyridine

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 114042-02-3, 5-Bromo-3-methyl-2-nitropyridine.

Reference:
Patent; Jiaxing Xiuzhou Qu Hong Hezhen Middle School; Zhu Shengxiang; (6 pag.)CN109456323; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-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, Computed Properties of C5H3Cl2N3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Cl2N3O2

(6) 2,4,6-trichloro-3-nitropyridine 2,6-dichloro-3-nitropyridine-4-amine (2.27 g, 10.9 mmol) was added to 48 mL concentrated hydrochloric acid, and cooled to 0-5 C. To the solution was added sodium nitrite (2.26 g, 32.7 mmol) in batches. After the addition of sodium nitrite, the reaction solution was stirred for 1 h at 0-5 C., and then stirred for 2 h at 25 C., adjusted to pH=7 with 40% sodium hydroxide solution, and extracted with ethyl ether. After the organic phase was dried (Na2SO4) and concentrated, it was subjected to column chromatography eluted with petroleum ether to afford 2 g white solid with a yield of 80.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; US2012/289497; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-04-7, 5-Bromo-3-chloropicolinaldehyde, 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: C6H3BrClNO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3BrClNO

5-Bromo-3-chloropicolylaldehyde 2.06 gAnd 1.00 g of 1-butylamineIn 10 ml of toluene,While performing azeotropic dehydration using a Dean-Stark tube,It was heated to reflux for 2 hours.Then,The solvent was distilled off under reduced pressure,To the residue was added acetic acid 10 mlAnd 1.05 g of nitroethane were added,Followed by stirring at 100 C. for 40 minutes.After completion of the reaction,The reaction mixture was allowed to cool to room temperature, 30 ml of water was added, and the mixture was extracted with ethyl acetate (50 ml × 2).The organic layers were combined, dried over anhydrous sodium sulfate and then saturated brine, dried,The solvent was distilled off under reduced pressure,The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 97)0.76 g of the objective compound was obtained as brown crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885168-04-7, 5-Bromo-3-chloropicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; nissan chemical industries, Ltd.; Takeshi, Mita; Yuki, Tajima; Yusuke, Nanya; Kosay, Iwasa; Makoto, Inada; Miho, Asahi; (124 pag.)JP2017/39722; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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, name: 2-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinonitrile

A suspension of 2-amino-5-bromo-3-pyridinecarbonitrile (0.59 g, 3 mmol), DMF-DMA (1 ml, 7.5 mmol), and MeCN (2 ml) was irradiated at 50 C (input power of: 200 W) for2 min. The resulting mixture was cooled to room temperature and poured onto ice cold water. The precipitate was filtered off, washed with water, and dried to afford (1E)-N?-(3-cyano-2-pyridinyl)-N,N-dimethylmethanimidamide (Lacbay et al. 2014). Light yellow solid; yield 95%; m.p. 116-117 C; 1H NMR (400 MHz, DMSO-d6) delta 8.65-8.60 (m, 1H, H-5), 8.46 (d, J = 2.6 Hz, 1H, H-3), 8.32 (d,J = 2.6 Hz, 1H, N=CH), 3.16 (s, 3H, CH3),3.07 (s, 3H,CH3); 13C NMR (100 MHz, DMSO-d6) delta 162.27 (C-2),157.00 (C=N), 153.23 (C-6), 144.32 (C-4), 116.77 (CN), 110.23 (C-5), 102.68 (C-3), 35.00 (C-N); IR (film): 3457(C-N), 3061, 2916, 2795, 2483, 2306, 2214 (CN), 1960, 1625 (C=N), 1562, 1395 cm-1; HRMS (ESI) m/z: calculatedfor C9H10BrN4+ [M + H]+: 253.0089; found: 253.0084.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Ya-Quan; Zong, Chao-Yang; Ji, Jin-Yu; Han, Qing; Chemical Papers; vol. 72; 12; (2018); p. 2965 – 2972;,
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.39903-01-0, name is 2-Amino-5-bromo-3-pyridinol, molecular formula is C5H5BrN2O, molecular weight is 189.01, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2O

Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39903-01-0, 2-Amino-5-bromo-3-pyridinol, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1235036-15-3, Adding some certain compound to certain chemical reactions, such as: 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate,molecular formula is C10H11BrClNO2, 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 1235036-15-3.

To Example 1.1.10 (100 mg) and tert-butyl3-bromo-6-chloropicolinate (52.5 mg) in dioxane(2 mL) was added tris(dibenzylideneacetone)dipalladium(O) (8.2 mg), K3P04 (114 mg), 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixturewas stirred at 95 oc for 4 hours, diluted with ethyl acetate and washed with water and brine. Theorganic layer was dried over Na2S04 , filtered, concentrated and purified by flash chromatography,eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to providethe title compound. MS (ESI) m/e 643.3 (M+Ht

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. 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; JUDD, Andrew, S.; PHILLIPS, Andrew, C.; SOUERS, Andrew, J.; BRUNCKO, Milan; (503 pag.)WO2017/214301; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Coupling: Example 24 is obtained as a white solid (40% yield) using acid C176 using Method C with non-critical changes. HRMS (FAB) calculated for C15H18N4O+H: 271.1559, found 271.1562 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (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. 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 6-Chloro-4-methylpyridin-3-amine

Compound 6-chloro-4-methylpyridin-3-amine la (568 mg, 4.0 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.22 g, 4.0 mmol), cesium carbonate (3.8 g, 12 mmol), [1,1′-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane adduct (146 mg, 0.2 mmol), 1,4-dioxane (30 mL), and water (7 mL) were mixed, degassed, and heated to reflux under nitrogen for 16 hrs. The mixture was cooled to room temperature and concentrated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 20/1 to 2/1) to produce the target compound tert-butyl 5-amino-4-methyl-5′,6′-dihydro-[2,3′-dipyridyl]-1′(2’H)-carboxylate 1b (401 mg, yellow oil), yield: 34%. MS m/z (ESI):290[M+1]

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, 66909-38-4, 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; Beijing InnoCare Pharma Tech Co., Ltd.; CHEN, Xiangyang; PANG, Yucheng; (44 pag.)EP3409672; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem