Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 67754-03-4, Methyl 2,5-dichloronicotinate, 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, 67754-03-4, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5Cl2NO2

Description 64: 1-(5-chloro-3-(methoxycarbonyl)pyridin-2-yl)azetidine-3- carboxylic acid (D64)To a mixture 3-Azetidinecarboxylic acid (41 1 mg, 4.06 mmol) and triethylamine (1 .17ml, 8.47 mmol) in methanol (3ml), methyl 2-chloropyridine-3-carboxylate (700 mg, 3.38 mmol) was added and the mixture was heated at 150C under microwave irradiation 10 min (2 cycles of 5 min each ). Solvents were evaporated in vacuo and the residue was taken in water (5ml) and 1 M HCI (5ml) and extracted with ethylacetate (3x5ml). Collected organics after solvent evaporation afforded the title compound (D64) (880 mg)MS: (ES/+) m/z: 270.8 [MH+] C1 1 H1 1 CIN204 requires 270.04 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.23 – 8.32 (m, 1 H) 7.90 – 8.06 (m, 1 H) 4.31 – 4.45 (m, 2 H) 4.17 – 4.30 (m, 2 H) 3.84 – 3.95 (m, 3 H) 3.58 (tt, J=8.93, 6.1 1 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67754-03-4, its application will become more common.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65-22-5, 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 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

2.2.1 PLSC·2H2O Semicarbazide hydrogenchloride (1.07 g, 10 mmol) was dissolved in warm H2O (10 mL), to which a warm solution of pyridoxal hydrogenchloride (2.00 g, 10 mmol) in H2O (10 mL) was added. To this solution Na2CO3·10H2O (3.00 g, 15 mmol) dissolved in H2O (10 mL) was added in portions, and the mixture was mildly heated for a couple of minutes. The obtained solution was left at room temperature for about 20 h, after which the single crystals were filtered and washed with H2O. Yield: 2.30 g (88%). Anal. Calc. for C9H16N4O5: C, 41.54; H, 6.20; N, 21.53. Found: C, 41.43; H, 6.16; N, 21.50%. Selected IR bands [ /cm-1]: 3466, 3381, nu(OH), nu(NH2); 3202, nu(NH); 2850, nu(NH+); 1697, 1678, nu(C=O); 1583, nu(CN); 1280, nu(COphenolic). UV-Vis (DMF) [lambdamax/nm (log epsilon/M-1 cm-1)]: 289 (4.12), 298sh (4.08), 327bp (3.75) (sh-shoulder, bp-broad peak).

According to the analysis of related databases, 65-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vojinovi?-Je?i?, Ljiljana S.; Jovanovi?, Ljiljana S.; Leovac, Vukadin M.; Radanovi?, Mirjana M.; Rodi?, Marko V.; Barta Hollo, Berta; Meszasaros Szecsenyi, Katalin; Ivkovi?, Sonja A.; Polyhedron; vol. 101; (2015); p. 196 – 205;,
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Pyridine | C5H5N – PubChem

Application of 87407-12-3 , The common heterocyclic compound, 87407-12-3, name is 3-(Trifluoromethyl)picolinic acid, molecular formula is C7H4F3NO2, 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.

A mixture of 3-trifluoromethyl-2-pyridine carboxylic acid (0.33 g, 1.6 mmol), (dimethylamino)-N,N-dimethyl(3H-[l,2,3]triazolo[4,5-]pyridin-3-yloxy)methaniminium hexafluorophosphate (i.e. HATU, 0.059 g, 1.6 mmol), and N,N-diisopropylethylamine (0.33 g, 2.6 mmol) were stirred in 10 mL dichloromethane. After 15 min, 2-[5-[3- (trifluoromethyl)-lH-pyrazol-l-yl]-2-pyrazinyl]benzenamine (i.e. the compound obtained in Example 3, Step C above) (0.4 g, 1.3 mmol) was added and the reaction was stirred at ambient temperature for approximately 16 h. The reaction mixture was then diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over Na2S04, evaporated under reduced pressure and then purified using silica gel column chromatography (20% ethyl acetate in petroleum ether as eluent) to yield 0.36 g of the title compound, a compound of the present invention. in NMR (400 MHz, dmso-d6) delta 12.20 (s, 1H), 9.31 (s, 1H), 9.05 (m, 2H), 8.91 (bs, 1H), 8.36 (m, 2H), 7.97 (d, 1H), 7.85 (m, 1H), 7.61 (t, 1H), 7.41 (t, 1H), 7.18 (d, 1H).

The synthetic route of 87407-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; TAGGI, Andrew, Edmund; KAR, Moumita; REDDY, Ravisekhara, P.; CAMPBELL, Mathew, James; WO2014/172190; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, 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, 5349-17-7, blongs to pyridine-derivatives compound. Product Details of 5349-17-7

General procedure: Potassium carbonate (418 mg, 3 mmol, 1 eq.) was added to a solution of malonitrile (200 mg, 3 mmol, 1 eq.) in dry DMF (5 mL). The reaction was stirred at room temperature for 1 hour and isopropyl isothiocyanate (311 mL, 3 mmol, 1 eq.) was added. After 1 hour stirring at room temperature, 2-bromo-1-(4-methoxyphenyl)ethan-1-one was added (687 mg, 3 mmol, 1 eq.) followed by potassium carbonate (418 mg, 3 mmol, 1 eq.). The mixture was further stirred for 15 hours, and poured into stirring ice/water (50 mL). The resulting precipitate was filtered and washed with water. The title compound was purified by recristalization from hexane/EtOAc and dried under vaccum (823 mg, yield: 87%, purity: 95.7%, Rt = 1.65 min. by method C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5349-17-7, its application will become more common.

Reference:
Article; Boutard, Nicolas; Sabiniarz, Aleksandra; Czerwi?ska, Klaudia; Jarosz, Ma?gorzata; Cierpich, Anna; Kolasi?ska, Ewa; Wiklik, Katarzyna; Gluza, Karolina; Commandeur, Claude; Buda, Anna; Stasiowska, Agata; Bobowska, Aneta; Galek, Mariusz; Fabritius, Charles-Henry; Bugaj, Marta; Palacz, Edyta; Mazan, Andrzej; Zar?bski, Adrian; Krawczy?ska, Karolina; ?urawska, Ma?gorzata; Zawadzki, Przemys?aw; Milik, Mariusz; W?grzyn, Paulina; Dobrza?ska, Monika; Brzozka, Krzysztof; Kowalczyk, Piotr; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 607 – 613;,
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.881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, molecular weight is 195.17, as common compound, the synthetic route is as follows.name: Dimethyl pyridine-2,5-dicarboxylate

To a solution of dimethyl pyridine-2,5-dicarboxylate 59-a (13.0 g, 66.6 mmol) in a mixture of THF (110 mL) and ethanol (110 mL) was added calcium chloride (29.6 g, 266 mmol). After stirring at room temperature for 30 minutes, the reaction was cooled to 0C, and sodium borohydride (3.78 g, 100 mmol) was added portion wise. After the addition was completed the reaction was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and dichloromethane were added, the organic layer was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to provide Intermediate 59-b as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,881-86-7, Dimethyl pyridine-2,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/74138; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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.

General procedure: For the synthesis of 3a and 3b, methods ofEmmereich et al. [1] were adapted as follows: Phenylboronic acid, 2-bromopyridine-4/5-carboxyaldehydeand sodium carbonate (2M) were dissolved in a 1:1 mixture of toluene andethanol (v/v, 10ml). The mixture was degassed for 10 minutes and thendichlorobis(triphenylphosphine)palladium(II) was added. The reaction mixturewas heated at 80 C for 5 h under argon atmosphere. The mixture was allowed tocool to room temperature and then organic molecules were extracted intodichloromethane (3×20 ml). Combined extracts were dried over sodium sulphateand then filtered. Upon concentration under reduced pressure crude product wasobtained as dark yellowish green liquid. Chromatography over silica-gel gavethe title compounds (3a and 3b) as liquid or solid. 2-pheny-4-formylpyridine (3a): A mixture of phenylboronic acid (197 mg, 1.6 mmol),2-bromopyridine-4-carboxyaldehyde 2a(200 mg, 1.1 mmol), sodium carbonate (2M, 0.5 ml) and dichlorobis(triphenylphosphine)palladium(II)(37.7 mg, 5%) gave 3a (152 mg,77%) as clear oil. Rf (Etil Asetat:Hekzan, 1:6 v/v) = 0.3. 1H NMR (600 MHz, CDCI3)delta(ppm): 10.14(s, 1H), 8.94 (d, J = 6 Hz, 1H), 8.13 (s, 1H), 8.06 (dd, J = 12Hz and 6 Hz, 2H) , 7.63 (d, J = 6 Hz, 1H), 7.53-7.43 (m,3H). 13C NMR (150 MHz, CDCI3) delta (ppm): 191.6, 159.1,151.1, 142.5, 138.2, 129.7, 128.9, 127.0, 120.5, 118,9.

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. 118289-17-1, 2-Bromopyridine-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alt?noelcek, Nuray; Aydemir, Murat; Tavasl?, Mustafa; Dos Santos, Paloma L.; Monkman, Andrew P.; Journal of Organometallic Chemistry; vol. 851; (2017); p. 184 – 188;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 871836-51-0 ,Some common heterocyclic compound, 871836-51-0, molecular formula is C6H4ClN3, 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.

Compound 1 (1.00 g, 6.5 mmol) was suspended in acetonitrile (100 ml), and sodium nitrite (339 mg, 8.5 mmol) was added thereto and reacted in an oil bath at 50 ° C. After 1 hour, the reaction mixture was cooled to room temperature, 2-deoxy-3,5-di-O- (p-toluyl) -alpha-D-ribofuranosyl chloride (2.66 g, 6.8 mmol) And the mixture was reacted at room temperature for 30 minutes. After filtration, the filtrate was concentrated under reduced pressure, the solvent was distilled off, the residue was adsorbed on a silica gel column, washed with a mixed solution of ethyl acetate and chloroform Eluting to give compound 2 (1.77 g, 54percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,871836-51-0, its application will become more common.

Reference:
Patent; NIHON UNIVERSITY; SAITOU, YOSHIO; SUZUKI, AZUSA; SAITOU, MIO; (41 pag.)JP2016/138078; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118289-17-1, 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde. A new synthetic method of this compound is introduced below.

To a chilled (-780C) solution of 2-bromo-pyridine-4-carbaldehyde (10.0 g, 53.8 mmol) in THF (100 mL) was added a 3 M solution of methylmagnesium chloride in THF (18 mL, 54 mmol) over a 10 minute period. After 1 hour, the yellow solution was allowed to warm gradually to room temperature over a 3 hour period. The reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford a brown oil. The crude material was purified by silica gel chromatography eluting with a gradient of 10-45% EtOAc in hexanes to afford l-(2- bromo-pyridin-4-yl)-ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105250-16-6, 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.105250-16-6, name is (2-Methylpyridin-4-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

To a stirred, ice-cooled solution of compound 66 (3.68 g, 16.4 mmol), prepared as described in US 6,720,328, in CH2CI2 (50 ml) was added ice-cold TFA (6.07 ml, 9.38 g, 82.1 mmol) via syringe over a period of ~1 min. The resultant clear yellow solution was stirred at 0 0C for 10 min, then at RT for 25h. Volatiles were removed under reduced pressure, and the residue was redissolved in CH2CI2 (35 ml). To this solution was added portionwise (exothermic) 7N methanolic ammonia (5 ml, 35 mmol), making the solution basic to pH paper and resulting in the formation of a precipitate. Solvent was removed under reduced pressure, and the residue was triturated with EtOAc (30 ml). The mixture was filtered, the filtrate was stripped of solvent under reduced pressure, and the residue was purified via flash chromatography on silica gel, eluting with CH2CI2-MeOH -NH3 (90:9:0.25), to obtain compound 67 as an off-white powder (1.43 g; 70percent).

The chemical industry reduces the impact on the environment during synthesis 105250-16-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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.60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, molecular weight is 152.581, as common compound, the synthetic route is as follows.

A solution of 4-chloro-1H-pyrrolo[3,2-c]pyridine(100 mg, 0.66 mmol) and 2,4-difluorophenol (213 mg, 1.64 mmol) in DMA (2 mL)was stirred for 5 minutes under nitrogen.Sodium hydride (26.2 mg, 0.66 mmol; 60% in mineral oil) was heated withstirring at 250 C for 3 minutes under microwave irradiation. The mixture was dilutedwith THF (10 mL) and quenched with water and ice (2 mL). The solution wasfiltered through a Varian ChemElute cartridge and concentrated to dryness. The materialwas partially purified by flash chromatography with gradient elution of heptaneand ethyl acetate (1:0 to 0:1) to give a gum. The material was further purifiedby reverse phase preparative HPLC to provide the desired product (49.0 mg, 60.7%) as a solid. HPLC purity: >99% (215nM), >99% (254 nM), >99% (280 nM). 1H NMR (400 MHz, DMSO-d6) d ppm 6.63 (dd, J=3.3, 1.0 Hz, 1 H) 7.08 – 7.19 (m, 2 H) 7.35 – 7.46(m, 3 H) 7.58 (d, J=5.9 Hz, 1 H). HRMS m/z calcd for C13H8F2N2O[M+H]+ 247.0677, found 247.0678.

Statistics shows that 60290-21-3 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[3,2-c]pyridine.

Reference:
Article; Hu, Yun-Jin; St.-Onge, Miguel; Laliberte, Sebastien; Vallee, Frederic; Jin, Shujuan; Bedard, Leanne; Labrecque, Jean; Albert, Jeffrey S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 14; (2014); p. 3199 – 3203;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem