Category: pyridine-derivatives

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. 393-53-3, name is 3-Fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Fluoroisonicotinic acid

3-Fluoroisonicotinic acid (3.00 g, 21.3 mmol) was dissolved in dioxane (6 mL), and then 30% methylamine aqueous solution (22.0 g, 213 mmol) was added. The reaction solution was heated to 140 C. and then stirred for 14 hours. Concentrated hydrochloric acid (12N, 3 mL) was added to adjust the pH value to pH=3, followed by filtration. The filter cake was dried to give 3-(methylamino)isonicotinic acid (3.00 g, yellow solid) with a yield of 93%. 1H NMR: (400 MHz, DMSO-d6) delta8.46 (s, 1H), 7.89 (s, 1H), 7.69 (d, J=4.8 Hz, 1H), 7.50 (d, J=4.8 Hz, 1H), 2.80 (s, 3H).

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, 393-53-3, 3-Fluoroisonicotinic acid.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Linyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (75 pag.)US2018/148451; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13472-85-0, Adding some certain compound to certain chemical reactions, such as: 13472-85-0, name is 5-Bromo-2-methoxypyridine,molecular formula is C6H6BrNO, 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 13472-85-0.

1.57 g K2CO3, 6.25 ml DMF was added sequentially to a flask equipped with a thermometer, a constant pressure dropping funnel,Stirring in a 100 ml three-necked flask, stirring, 1.41 ml of 5-bromo-2-methoxypyridine slowly,After completion of the dropwise addition, 2.07 g of bisulfonamide was slowly added and the mixture was stirred for 2 hours.Add 1.7 g of 2-chloropyridine stirring reaction 3 hours, diluted with water, stirring 20 min, liquid;The aqueous phase was extracted with ethyl acetate, the organic phases were combined, washed twice with saturated brine,Concentrated under reduced pressure to give a piranone intermediate yellow oil with a purity of 83% and a yield of 85%.

According to the analysis of related databases, 13472-85-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Venturefarm Biotech Corp.; Chen, Mengnan; Zhao, Guolei; (4 pag.)CN105906557; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98400-69-2, 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 98400-69-2 as follows.

REFERENTIAL EXAMPLE 2 tert-Butyl 3-sulfanylpyridin-4-ylcarbamate: The compound (61.6 g) obtained in Referential Example 1 was dissolved in tetrahydrofuran (2,000 ml), and the solution was stirred at -78¡ã C. for 10 minutes. A hexane solution (1.59 mol/l, 500 ml) of n-butyllithium was added dropwise to the solution, and the mixture was stirred for 10 minutes and then for 2 hours with ice cooling. After the reaction mixture was cooled to -78¡ã C., sulfur powder (12.2 g) was added, and the resultant mixture was warmed to room temperature and stirred for 1 hour. Water (1,000 ml) was added to the reaction mixture to separate a water layer. After 3N hydrochloric acid was added to the water layer to adjust the pH of the water layer to 3 to 4, methylene chloride was added to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride_methanol=50:1) to obtain the title compound (33.2 g). 1H-NMR (DMSO-d6) delta: 1.52(9H,s), 7.89(1H,d,J=6.4 Hz), 7.99(1H,d,J=6.4 Hz), 8.20(1H,s), 9.91(1H,br.s). MS (FAB) m/z: 227(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98400-69-2, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18617-50-0 , The common heterocyclic compound, 18617-50-0, name is Ethyl 6-hydroxynicotinate, molecular formula is C8H9NO3, 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.

Stage 1 : A mixture of {4-[(4-{[(tert-butoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}boronic acid (800mg; 2.39 mmol; prepared as described for the synthesis of intermediate X.7 without BOC deprotection step), ethyl 6-hydroxypyridine-3-carboxylate (420 mg; 2.51 mmol), copper(II) acetate (250 mg; 1.38 mmol) and pyridine (210 muIota; 2.60 mmol) in DCM (10 ml) is stirred overnight. The mixture is filtered and extracted with water. The organic layer is dried with sodium sulphate, filtered and evaporated. The residue is purified by silica gel column chromatography (gradient DCM / methanol 98:2 94:4) to yield ethyl 1-{4-[(4-{[(tert-butoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}-6-oxo-1,6-dihydropyridine-3-carboxylate. Yield: 580 mg (53percent of theory). C25H33N3O5. ESI Mass spectrum: m/z = 456 [M+H]+.

The synthetic route of 18617-50-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; BLUM, Andreas; HAMPRECHT, Dieter; KLEY, Joerg; WO2013/92674; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 71255-09-9 ,Some common heterocyclic compound, 71255-09-9, molecular formula is C7H7NO2, 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.

Part F: 2-(4-(2-(2-methoxypyridin-3-yl)-7-methyl-3H-benzo[d]-imidazol-5-yl)piperidin-1-yl)-N-methylethanamine (Example 2); A mixture of tert-butyl 2-(4-(3,4-diamino-5-methylphenyl)piperidin-1-yl)ethyl(methyl)carbamate (0.11 mmol) and 2-methoxynicotinaldehyde (15 mg, 0.11 mmol) in methanol (5 mL) was heated at 60 C. for 4h. solvent was evaporated and the crude intermediate was then treated with TFA in 1,2-dichloroethane (25%, 1 mL) at rt for 2 h. solvent was evaporated and the residue was purified by prep-HPLC to give 2-(4-(2-(2-methoxypyridin-3-yl)-3H-benzo[d]imidazol-5-yl)piperidin-1-yl)-N-methylethanamine as a brown oil (11 mg, 27% yield). MS (ESI) m/z 380.22 (M+H) 1H NMR (CD3OD) delta 8.54 (dd, 1H, J=5.0, 1.7 Hz), 8.48 (dd, 1H, J=7.7, 1.7 Hz), 7.84 (d, 1H, J=8.1 Hz), 7.81 (s, 1H), 7.61 (dd, 1H, J=7.6, 1.1 Hz), 7.33 (dd, 1H, J=7.7, 4.4 Hz), 4.25 (s, 3H), 3.80 (d, 2H, J=12.1 Hz), 3.58 (s, 3H), 3.31 -3.15 (m, 3H), 2.82 (s, 3H), 2.32-2.17 (m, 7H).

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. 71255-09-9, 2-Methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Purandare, Ashok Vinayak; Wan, Honghe; Huynh, Tram N.; US2006/235037; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86129-63-7 ,Some common heterocyclic compound, 86129-63-7, molecular formula is C9H9Cl2NO2, 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.

Step 3. Preparation of 2-chloro-4-methoxy-6-methyl-nicotinic acid ethyl ester (B17-3): A solution of B17-2 (30 g, 128.2 mmol) in methanol (102 mL) was cooled to 0 C. and treated portion-wise over 30 minutes with NaOMe (8.5 g, 157.4 mmol). The reaction mixture was then heated at 60 C. for 5 hours. The reaction mixture was cooled to 25 C., filtered, and concentrated. The resultant residue was diluted with DCM (350 mL), filtered through a Celite bed, and washed with DCM. The combined filtrates were concentrated, and the resultant residue was purified by chromatography (silica gel; 6% EtOAc in petroleum ether as eluting solvent) to provide B17-3 as a pale yellow solid. Yield: 20.62 g, 70%. 1H NMR (CDCl3): delta 6.66 (s, 1H), 4.4 (q, 2H), 3.95 (s, 1H), 3.92 (s, 3H), 2.52 (s, 3H) and 1.38 (t, 3H). Mass: (M+1) 230 calculated C10H12ClNO3.

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. 86129-63-7, Ethyl 2,4-dichloro-6-methyl-3-pyridinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US2009/54395; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113682-56-7 ,Some common heterocyclic compound, 113682-56-7, molecular formula is C16H12N2, 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.

0.02 mmol of copper nitrate trihydrate was dissolved in 2 mL of dimethylformamide,Placed in a glass test tube having a diameter of 5 mm,A solution of 0.01 mmol of terephthalic acid and 0.02 mmol of 4,4 ‘- (1,4-phenylene) dipyridine in 2 mL of methanol was gently laminated thereon,The glass test tube was placed in a container containing buffer material so as not to give vibration for 14 days and it was left to stand.Synthesis was carried out in the same manner as in Example,A single crystal was not obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113682-56-7, its application will become more common.

Reference:
Patent; NIPPON STEEL & SUMITOMO METAL CORPORATION; KYOTO UNIVERSITY; KAJIRO, HIROSHI; TOKUMARU, SHINJI; KITAGAWA, SUSUMU; MATSUDA, RYOTARO; SATO, HIROSHI; JEON, HYUNG JOON; (25 pag.)JP2016/20318; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-48-4, 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 6959-48-4 as follows.

Step C: Preparation of Diethyl 2-(1-(pyridin-3-yl)propan-2-yl)malonate. To a suspension of diethyl methyl malonate (1.80 g, 10.2 mmol) in DMF (25 ml) at 0 C. was added sodium hydride (1.25 g, 31.0 mmol, 60%), followed by 3-(chloromethyl)pyridine hydrochloride (2.00 g, 12.2 mmol) and stirred for 8 h at room temperature. The reaction mixture was quenched with acetic acid and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 2.50 g (91.2%) of diethyl 2-(1-(pyridin-3-yl)propan-2-yl)malonate as pale brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6959-48-4, its application will become more common.

Reference:
Patent; Zeitlmann, Lutz; Niestroj, Andre; Heiser, Ulrich; US2011/224225; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13472-61-2, Adding some certain compound to certain chemical reactions, such as: 13472-61-2, name is 5-Iodo-2-methoxypyridine,molecular formula is C6H6INO, 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 13472-61-2.

To a 25-mL flask equipped with a magnetic stir bar and a condenser crowned with argon balloon, charged with a mixture of anhydrous DMF (4 mL) and 5-iodo-2-methoxypyridine (0.99 g, 0.042 mmol), degassed for 2 h using a stream of argon slowly bubbled through the solution at rt. during vigorous stirring, phenylacetylene (0.055 mmol), Pd(PPh3)2Cl2 (38 mg), CuI (8 mg) were added. Subsequently anhydrous Et3N (1.5 mL) was added over 10 minutes and the mixture was heated at 50 C for 90 minutes. After this time the reaction mixture was cooled to rt. and aqueous saturated NaCl (10 mL) was added, the mixture was extracted with ethyl acetate (3 x 50 mL) and the combined organic layers were washed with brine (5 mL), dried over MgSO4 and filtered through the pad of Celite. Concentration in vacuo and purification by flash column chromatography (silica gel, n-hexane : ethyl acetate 9 : 1) yielded 1d in 90% yield as colourless oil.

According to the analysis of related databases, 13472-61-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sos?nicki, Jacek G.; Struk, ?ukasz; Idzik, Tomasz; Maciejewska, Gabriela; Tetrahedron; vol. 70; 45; (2014); p. 8624 – 8635;,
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.130721-78-7, name is tert-Butyl (4-chloropyridin-2-yl)carbamate, molecular formula is C10H13ClN2O2, molecular weight is 228.68, as common compound, the synthetic route is as follows.Formula: C10H13ClN2O2

To a stirred solution of compound 5-(5- chloro-2-fluorophenyl)-6-methoxy-N2,N2-dimethylpyridine-2, 3-diamine (0.5 g, 1.69 mmol, 1.0 eq) and tert-butyl (4-chloropyridin-2-yl)carbamate (0.463 g, 2.02 mmol, 1.2 eq) in dioxane (20 mL) was added Cs2C03 (2.20 g, 6.76 mmol, 4.0 eq) at rt. The resulting mixture was purged with nitrogen for 10 min followed by addition of Pd2(dba)3 (0.185 g, 0.20 mmol, 0.12 eq) and xantphos (0.146 g, 0.25 mmol, 0.15 eq), again purged with nitrogen for 10 min. The reaction mixture was heated at l30C for 48 h. The progress of reaction was monitored by LCMS. The reaction mixture was filtered through celite, the residue was washed with EtOAc (10 mL). The filtrate was concentrated and purified by combi flash chromatography [silica gel 100-200 mesh; elution 0-10 MeOH in DCM] to afford the desired compound (150 mg, 22.83%) as brown solid. LCMS: (M+l)+ 388.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130721-78-7, tert-Butyl (4-chloropyridin-2-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; INTEGRAL BIOSCIENCES PVT. LTD.; PUJALA, Brahmam; PENDHARKAR, Dhananjay; AGARWAL, Anil Kumar; KUMAR, Varun; ARYA, Satish Kumar; CHAKRAVARTY, Sarvajit; (0 pag.)WO2020/12357; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem