Category: pyridine-derivatives

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. 19798-80-2, name is 4-Chloropyridin-2-amine. A new synthetic method of this compound is introduced below., Formula: C5H5ClN2

Step 1 : To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 C for 3 hours then poured into ice- water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2S04) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2 -amine (460 mg, 16%) as a yellow solid MS ESI calcd for C6H8N20 [M + H]+ 125, found 125.

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, 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ROMEO, Eric Thomas; MACHACEK, Michelle, R.; TROTTER, Benjamin Wesley; MILLER, Thomas Allen; ANDRESEN, Brian Michael; ANTHONY, Neville John; TAOKA, Brandon, M.; LIU, Yuan; WO2012/151137; (2012); 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. 891785-18-5, name is 3-(Benzyloxy)-5-bromo-2-chloropyridine, molecular formula is C12H9BrClNO, 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. Computed Properties of C12H9BrClNO

To a suspension of 68 3-(benzyloxy)-5-bromo-2-chloropyridine (25.7 mg, 86.0 mmol) and 41 potassium phosphate (54.9 g, 259 mmol) in 9 tetrahydrofuran (180 mL) were added successively 14 water (130 mL), 17 (E)-2-(3-methoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.1 mL, 95.0 mmol) and [1,1?-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (3.54 g, 4.33 mmol), and the mixture was stirred at room temperature for 2 hr. [1,1?-Bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (1.70 g, 2.04 mmol) was added again thereto, and the mixture was stirred at room temperature for 3 hr, warmed to 33 C., and stirred for 1 hr. The reaction solution was diluted with ethyl acetate (180 mL), and the insoluble substance was removed by filtration. The organic layer of the filtrate was washed with water and saturated brine, silica gel (50 g) was added thereto, and the mixture was stirred at room temperature for 1 hr. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=15:1 to 4:3) to give 70 (E)-3-(benzyloxy)-2-chloro-5-(3-methoxyprop-1-en-1-yl)pyridine (20.9 g, yield 83%). 1H-NMR (DMSO-D6) delta: 3.29 (3H, s), 4.06-4.07 (2H, m), 5.29 (2H, s), 6.59-6.60 (2H, m), 7.32-7.49 (5H, m), 7.81 (1H, d, J=1.8 Hz), 8.02 (1H, d, J=2.1 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 891785-18-5.

Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); 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. 13959-02-9, name is 3-Bromoisonicotinic acid, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H4BrNO2

A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62%) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).

The synthetic route of 13959-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56129-55-6, Adding some certain compound to certain chemical reactions, such as: 56129-55-6, name is 1-(Pyridin-3-yl)ethanamine,molecular formula is C7H10N2, 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 56129-55-6.

General procedure: To a solution of ethyl 2- chlorothieno[3,2-(/Jpyrimidine-4-carboxylate (100 mg, 0.41 mmol) and DIEA (0.22 mL, 1.23 mmol) in NMP (3 mL) was added (6-methoxypyridin-3-yl)methanamine hydrochloride (commercially obtained from PharmaBlock, Sunnyvale, CA) (97 mg, 0.89 mmol). The reaction mixture was stirred at 130 C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with 25% aqueous NaCl solution, then with brine three times and dried. The solvent was evaporated and the residue was purified by flash chromatography (24g, HP silica, Teledyne Isco) eluting with 2% to 100% solvent A (DCM/MeOH/NH4OH, 100/10/1) in DCM to provide 2-chloro-N-((6-methoxypyridin-3- yl)methyl)thieno[3,2-Patent; CORVUS PHARMACEUTICALS, INC.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; BRADLEY, Erin, Kathleen; VERNER, Erik; (816 pag.)WO2019/46784; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-63-3, 2-Chloro-6-methylpyridine, 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, Application In Synthesis of 2-Chloro-6-methylpyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Chloro-6-methylpyridine

Intermediate 691 ,1 -Dimethylethyl r2-(4-{(2S,4/?)-1 -acetyl-2-methyl-4-r(6-methyl-2-pyridinyl)aminol-1 ,2,3,4- tetrahvdro-6-quinolinyl)-1 /-/-pyrazol-1 -yl)ethyllmethylcarbamateA flask was charged with 2-chloro-6-methylpyridine (141 mg, 1 .103 mmol) and treated at room temperature under nitrogen with 1 ,1 -dimethylethyl [2-(4-{(2S,4/?)-1 -acetyl-2-methyl- 4-amino-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 -yl)ethyl]methylcarbamate (for a preparation see intermediate 55) (228 mg, 0.551 mmol) in 1 ,4-dioxane (5 mL). 2′- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (43.4 mg, 0.1 10 mmol), sodium tert-butoxide (106 mg, 1 .103 mmol) and tris(dibenzylideneacetone)dipalladium(0) (50.5 mg, 0.055 mmol) were added and the resulting mixture was stirred at 1 10C for 16 h then cooled to room temperature and partitioned between AcOEt (25 mL) and water (25 ml_). The layers were separated and the organic phase was washed with water (25 mL) then dried over Na2S04 and concentrated in vacuo. Purification of the residue on SP4 using a 50 G silica cartridge (gradient: 1 to 5% MeOH in DCM) gave 1 ,1 -dimethylethyl [2-(4-{(2S,4R)-1 -acetyl-2- methyl-4-[(6-methyl-2-pyridinyl)amino]-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 – yl)ethyl]methylcarbamate (107.9 mg, 0.198 mmol, 35.8 % yield) as a brown oil.LCMS (Method B): Retention time 0.79 min, [M+H]+ = 519.20

The synthetic route of 18368-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GOSMINI, Romain, Luc, Marie; WO2011/54848; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 137628-17-2, 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. 137628-17-2, name is 2,3-Dibromo-5-chloropyridine, molecular formula is C5H2Br2ClN, 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 solution of compound 47.1 (10.0 g, 37.19 mmol) in THF (100 ml) was added slowly asolution of isopropylmagnesium chloride/lithium chloride (1.3 M in THF, 31 ml, 40.3 mmol)at -40 C. The solution was stirred for 30 mm at -40 C and DMF (8.5 ml, ill mmol) wasadded. The resulting solution was warmed to room temperature and stirred for 30 mm. Thereaction was quenched with 1M HCI (70 ml) and diethyl ether (60 ml) was added. The organic layer was separated and washed with 5% aqueous NaHCO3. The solvent was removed under vacuum. The resulting solids were dissolved in methanol (90 ml). Thesolution was cooled to 0 C NaBH4 (3.60 g, 95.2 mmol) was slowly added. The reaction mixture was stirred for 30 mm, then quenched with water (30 ml). The resulting mixture was concentrated under vacuum to approximately 40 ml. The resulting suspension was stirred vigorously at room temperature for 1 h and the solids were collected by filtration and driedin a vacuum to give compound 47.2 (7.20 g, 88%) as a colourless solid. 1H NMR (ODd3,400 MHz) O 2.33 (t, 1H), 4.73 (d, 2H), 7.88 (d, 1H), 8.26 (d, 1H). LCMS (221.9 [M+H]).

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 137628-17-2, 2,3-Dibromo-5-chloropyridine.

Reference:
Patent; THE UNIVERSITY OF SHEFFIELD; RICHARDS, Gareth; SKERRY, Timothy, M.; HARRITY, Joseph, P.A.; ZIRIMWABAGABO, Jean-Olivier; TOZER, Matthew, J.; GIBSON, Karl, Richard; PORTER, Roderick, Alan; BLANEY, Paul, Matthew; GLOSSOP, Paul, Alan; (369 pag.)WO2018/211275; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, 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: C8H7NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C8H7NO3

Reference Example 28 Methyl 6-(2-tert-butyl-5-chloro-6-methoxy-1H-indol-3-ylmethyl)pyridine-2-carboxylate To a solution of triethylsilane (0.202 mL) and trifluoroacetic acid (0.049 mL) in dichloromethane (2 mL) was added a suspension of 2-tert-butyl-5-chloro-6-methoxy-1H-indole (100 mg) and methyl 6-formylpyridine-2-carboxylate (76.2 mg) in dichloromethane (1.5 mL) under ice-cooling, and this mixture was stirred at room temperature overnight. To the reaction mixture was added water, and then the resulting mixture was alkalified by the addition of sodium hydrogen carbonate. The organic layer was separated and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (152 mg). 1H-NMR (CDCl3) delta ppm: 1.39 (9H, s), 3.90 (3H, s), 4.05 (3H, s), 4.52 (2H, s), 6.91 (1H, s), 6.95-7.05 (1H, m), 7.28 (1H, s), 7.60 (1H, t, J=7.8 Hz), 7.80-8.20 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189278-27-1, 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 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-6-(trifluoromethyl)pyridine (200 mg, 0.885 mmol) in a solvent mixture of toluene (1.5 ml)/water (1.5 ml)/ethanol (0.7 ml) was added 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine (200 mg, 0.738 mmol), cesium carbonate (601 mg, 1.844 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (30.3 mg, 0.037 mmol). The reaction mixture was heated in a benchtop microwave at 120 C. for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The organics were dried with MgSO4, filtered and then concentrated in vacuo. The residue was purified by column chromatography, eluting with 0-50% acetone in hexanes to afford 2-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)-6-(trifluoromethyl)pyridine as a white solid (82 mg, 38.3%): mp 130-131 C.; 1H NMR (400 MHz, acetone-d6) delta 9.24 (d, J=2.4 Hz, 1H), 9.13 (d, J=0.5 Hz, 1H), 8.60 (dd, J=4.7, 1.4 Hz, 1H), 8.44 (s, 1H), 8.35 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 8.12 (qd, J=8.3, 4.7 Hz, 2H), 7.72 (dd, J=7.1, 1.5 Hz, 1H), 7.59 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 290.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); 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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, molecular formula is C8H10ClNO3, 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. Recommanded Product: 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

H2L2 was prepared by stirring 2-aminophenol (0.218 g, 2.00 mmol) dissolved in 6 mL of methanol/KOH pH ca. 9.0 and pyridoxal hydrochloride (0.407 g, 2.00 mmol) in 8 mL methanol, at room temperature for 3 h. After cooling the mixture was kept at 4 C overnight and the orange solid was filtered, washed with water, cold methanol and diethyl ether and dried under vacuum. Yield: 85%, 0.390 g. MM (C14H14N2O3) = 258.3 g/mol. Elemental Analysis: Calc. forC14H14N2O3: C, 65.11; H, 5.46; N, 10.85; Found: C, 64.9; H, 5.7; N,10.7. ESI-MS: m/z [Found (Calcd)]: 259.15 (259.3) (100%) [L+H]+;257.11 (257.29) (100%) [L-H]-. UV-Vis in dmso, lambdamax/nm (epsilon/M-1cm-1): 295 (8282), 360 (11601), 463 (421); 1H NMR (dmso-d6, delta/ppm): 2.55 (s, 3H, H17); 4.89 (s, 2H, H18); 6.97 (t, 1H, H2); 7.07 (d, 1H,H6); 7.28 (t, 1H, H1); 7.69 (d, 1H, H3); 7.98 (s, 1H, H12); 9.30 (s, 1H,H9); 5.63 (s, 1H, R-OH) and 10.45 (s, 1H, Ar-OH). 13C NMR (dmso-d6,delta/ppm): 16.15 (C17); 57.83 (C18); 116.82 (C6); 119.64 (C2); 119.73(C3); 121.82 (C11); 129.43 (C12); 130.45 (C1); 131.30 (C4); 136.82(C10); 147.13 (C14); 151.98 (C15); 156.28 (C9) and 157.82 (C5).LogP = 2.21 [24].

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Cavaco, Isabel; Correia, Isabel; Costa Pessoa, Joao; Marques, Fernanda; Nunes, Patrique; Inorganica Chimica Acta; vol. 507; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1681-37-4 ,Some common heterocyclic compound, 1681-37-4, molecular formula is C5H5N3O2, 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.

To a solution of 4-amino-3-nitropyridine (2.0 mmol) in DMF (10 mL), NaH (2.2 mmol) was addedslowly, the mixture was stirred at room temperature for 30 min. Then ethyl iodine (2.0 mmol) wasadded slowly into the mixture until the reaction is finished monitored by TLC. Then the solvent wasevaporated and the residue was purified by silica gel chromatography by DCM/MeOH system toafford 4-ethylamino-3-nitropydine.To a solution of 4-ethylamino-3-nitropydine (1.0 mmol) in EtOH (10 mL), 10% Pd/C was added.Then the mixture was reduced by catalytic hydrogenation. Until the completion of the reaction,the Pd/C was filtered and the solvent was evaporated. The product was used in the next step withoutfurther purification.The solution of substituted 4-ethylamino-3-aminopydine (0.5 mmol), benzaldehyde (0.5 mmol)with sodium pyrosulfite (0.5 mmol) was stirred in DMF (8 mL) under 120 C overnight. On completionof the reaction, the solvent was evaporated and the residue was purified by silica gel chromatographyby DCM/MeOH system to afford the final product. If necessary, the crude product could berecrystallized in DCM to afford pure compound [31].

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. 1681-37-4, 4-Amino-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Liangkun; Hang, Nan; Zhang, Chao; Chen, Yu; Li, Shuchun; Sun, Yang; Li, Zhongjun; Meng, Xiangbao; Molecules; vol. 22; 2; (2017);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem