Pyridine-derivatives

Synthetic Route of 122851-69-8, 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. 122851-69-8, name is 3-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

A solution of cis-4-(2,3,6-trifluorophenyl)cyclohexanol (3.66 g) in THF (100 ml)was cooled to 0C, 60% sodium hydride (1.272 g) was added, and the mixture wasstirred under a calcium chloride tube dry atmosphere at room temperature for 10 min.To the reaction mixture was added 3-bromo-2-(chloromethyl)pyridine (4.92 g), and themixture was stirred at 70C for 3 hr. Water was added to the mixture at room temperature,and the mixture was extracted with ethyl acetate. The organic layer waswashed with saturated brine, dried over anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The residue was purified by silica gel chromatography(ethyl acetate/hexane) to give the title compound (3.73 g).MS, found: 401.0,403.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,122851-69-8, 3-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58539-65-4, 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. 58539-65-4, name is 2-Methylnicotinamide. A new synthetic method of this compound is introduced below.

Step 2 Preparation of 3-cyano-2-methylpyridine: To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0 C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75%): mp(DSC) 56-58 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; GD Searle & Co; US5616601; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Intermediate 80: N-(4-(2-(Hydroxymethyl)-5-methyl-4-oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide. 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolane (1 1.13 mL, 77 mmol) was added to a mixture of 7-bromo-2- (hydroxymethyl)-5-methylfuro[3,2-c]pyridin-4(5/-/)-one (for a preparation see Intermediate 78, 3.3 g, 12.79 mmol) and triethylamine (10.71 mL, 77 mmol) in 1 ,4-dioxane (20 mL) and the mixture was stirred for 5 min under nitrogen. Pd(PPh3)4 (1.478 g, 1 .279 mmol) was added and the mixture heated to 100C for 18 h. The mixture was cooled in an ice bath, then isopropanol (20.00 mL) was added, initially very cautiously, followed by water (10 mL), potassium carbonate (5.30 g, 38.4 mmol), PEPPSI-SIPr (0.871 g, 1.279 mmol) and A/-(4-bromopyridin-2-yl)acetamide (for a preparation see Intermediate 79, 3.02 g, 14.07 mmol). The mixture was heated to 80C for 2 h under nitrogen, then allowed to stand over the weekend. The mixture was diluted with ether (100 mL) and stirred for 10 min, then filtered and the solid was washed with water (50 mL) and dried under vacuum for 10 min to give the crude product. The resulting solid was heated in methanol (50 mL) to reflux, then cooled in an ice bath and the solid product collected by filtration to give A/-(4-(2-(hydroxymethyl)-5-methyl-4- oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide (2.76 g, 8.81 mmol, 68.9 % yield) as a colourless solid. 1H NMR (400MHz, DMSO-of6) delta-ppm 10.53 (1 H, s), 8.50 (1 H, s), 8.38 (1 H, d), 8.13 (1 H, s), 7.48 (1 H, m), 6.85 (1 H, s), 5.46 (1 H, m), 4.55 (2H, d), 3.61 (3H, s), 2.13 (3H, s). LCMS (2 min, Formic): Rt = 0.55 min, MH+ 314.

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); 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

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

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

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

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

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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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. Formula: C6H6F3N3

To a stirred solution of l-(4-(3-cyanobenzamido)phenyl)cyclobutanecarboxylic acid (65 mg, 0.20 mmol) in pyridine (2 mL) was added EDC (97 mg, 0.51 mmol) and 5- (trifluoromethyl)pyridine-2,3-diamine (30 mg, 0.17 mmol) at RT. After the addition was finished, the mixture was stirred at 40 C for 16 h. The reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by reversed phase HPLC, eluting with water (0.1%TFA)-ACN to give te title compound. MS (EI) m/z 480 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 107867-51-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 142896-15-9, 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 142896-15-9, name is Methyl 2,6-dimethylisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1.372 g (8.3 mmol) of (3), 60 mg of AlBN and 2.866 g (16.1 mmol) of NBS in 120 ml of CCl4 is refluxed under a nitrogen atmosphere and under irradiation with a 100 W lamp, for 8 hours. The reaction medium is then returned to room temperature, after which it is washed with 200 ml of saturated NaHCO3 solution. After removing the lower phase (CCl4), the aqueous phase is extracted 4 times with 50 ml of CHCl3; the combined organic extracts are then washed with 100 ml of H2O, dried (Na2SO4) and then concentrated to dryness. Purification of the residue obtained by chromatography on silica [gradient: cyclohexane-CH2Cl2 (80/20) to pure CH2Cl2) makes it possible to separate out a first fraction of the bromo derivative (4), from the polybromo species, from a mixture of isomers of symmetrical and asymmetrical dibromo derivatives and from the monobromo species also formed. [0153] In order to have available a larger amount of methyl 2,6-dibromomethyl isonicotinate, the monobromo compound isolated above [0.543 g (2.2 mmol)] is mixed with 0.4 g (2.2 mmol) of NBS, 23 mg of AIBN and 50 ml of CCl4 and is then treated under the above bromination conditions to give a second fraction of (4). [0154] Finally, a purification by chromatography on silica [gradient: pure cyclohexane to cyclohexane/EtOAc (85/15)] of the mixtures of dibromoisomers, isolated in the above two reactions, gives a final fraction of (4), i.e. 596 mg in total (22%). [0155] m.p.: 90-92 C. [0156] TLC: Rf: 0.6 (SiO2/CH2Cl2) [0157] HPLC: Tr: 20 min 5 sec [0158] UV: CHCl3: 290.8 nm (4270); 240.3 nm (3010) [0159] NMR: 1H CDCl3; internal reference TMS [0160] 3.98 (s, 3H, CH3); 4.58 (s, 4H, CH2); 7.92 (s, 2H, Py) [0161] 13C CDCl3; internal reference 77.0 ppm [0162] 32.8 (CH2); 52.9 (OCH3); 122.2 (Ct); 139.8, 157.9 (Cq); [0163] 164.7 (CO). [0164] MS (EI): 322.9 (M+, 15); 243.9 (M+-Br, 100); 163 (M+-2Br, 15.7). [0165] MA: C9H9NO2Br2 (322.98) [0166] Calculated: C 33.47H 2.80 N 4.33 O 9.90 [0167] Found: C 33.69H 2.81 N 4.29 O 10.17

According to the analysis of related databases, 142896-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Autiero, Herve; Bazin, Herve; Mathis, Gerard; US2004/92726; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem