Month: April 2022

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.1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, molecular weight is 239.58, as common compound, the synthetic route is as follows.Formula: C8H5ClF3NO2

Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80 C. for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (EI): m/e=262.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21901-41-7, 2-Hydroxy-4-methyl-5-nitropyridine, 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, 21901-41-7, blongs to pyridine-derivatives compound. Quality Control of 2-Hydroxy-4-methyl-5-nitropyridine

EXAMPLE 12 5-Methoxypyrrolo[2,3-c]pyridine (Compound 9) A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours. The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride. The residual oil then passed througha silica gel filter (dried at 150 C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1). This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95%) as an orange oil, which crystallized below 0 C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1; 1 H NMR (CDCl3) delta 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21901-41-7, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5051412; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7477-10-3 , The common heterocyclic compound, 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, molecular formula is C6H3ClN2O4, 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: A solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid. 4.2.4.3 6-(Benzylethylamino)-5-nitronicotinic acid (6c) Procedure A was used with compound 5 (405 mg, 2.0 mmol) and benzyl-ethyl-amine (540 mg, 4.0 mmol) to afford product 6c as a yellow solid (428 mg, 71%). 1H NMR (300 MHz, CDCl3) delta: 8.93 (s, 1H), 8.65 (s, 1H), 7.32-7.21 (m, 5H), 4.85 (s, 2H), 3.48 (q, J = 6.9 Hz, 2H), 1.22 (t, J = 6.9 Hz, 3H). ESI-MS: m/z (300, MH-).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18699-87-1, 2-Methyl-3-nitropyridine, 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 C6H6N2O2, blongs to pyridine-derivatives compound. Computed Properties of C6H6N2O2

Step 2: 2-bromomethyl-3-nitropyridine; 2,2′-Azobis(isobutyronitrile) (2.7 g, 16.4 mmol) was added to a solution of2-methyl-3-nitropyridine (12.97 g, 92.6 mmol) prepared in Step 1 and N- bromo-succinimide (23.06 g, 130 mmol) in carbon tetrachloride (100 ml). The reactionmixture was refluxed for 3 days, cooled to room temperature, and then concentratedunder reduced pressure. The resulting residue was diluted with ethyl acetate (100 ml)and then washed with a saturated sodium bicarbonate solution and a saturated sodiumthiosulfate solution. The organic layer was dried on anhydrous magnesium sulfate andthen purified with purified with silica gel column chromatography(dichloromethane/n-hexane=2/l, v/v) to give 7.5 g of the titled compound as brown oil.lH-NMR(400MHz, CDCy 5 8.82(d, 1H), 8.39(d, 1H), 7.56(t, 1H), 5.07(s, 2H)

The synthetic route of 18699-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; JANG, Sun-Young; WO2006/25717; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1346148-32-0 ,Some common heterocyclic compound, 1346148-32-0, molecular formula is C8H8FNO2, 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.

b) 5-Fluoro-3-methyl-pyridine-2-carboxylic acid To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) in MeOH (6 ml) was added at 22 C. a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HCl. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z=153.7 [M-H]-.

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. 1346148-32-0, Methyl 5-fluoro-3-methylpicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banner, David; Guba, Wolfgang; Hilpert, Hans; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Rogers-Evans, Mark; Rombach, Didier; Woltering, Thomas; Wostl, Wolfgang; US2011/312937; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54232-43-8, 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. 54232-43-8, name is 6-Bromo-5-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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.

A mixture of 6-bromo-5-methoxy-pyridine-2-carboxylic acid (0.3 g, 1 mmol), 3- chlorophenylboronic acid (CAN 63503-60-6, 0.23 g, 1 mmol), tris(dibenzylideneacetone)- dipalladium(0) (CAN 52409-22-0, 0.12 g), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (CAN 161265-03-8, 0.15 g) and potassium carbonate (0.21 g, 2 mmol) in 1,4-dioxane (10 mL) was stirred for 12 h at 110C under a nitrogen atmosphere. The reaction mixture was filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride) to give the title compound (0.1 g, 29%); MS (EI): m/e = 264.0[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 54232-43-8, 6-Bromo-5-methoxypicolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.Recommanded Product: 131747-62-1

General procedure: A solution of lithium hydroxide (0.8 mg, 0.03 mmol) and 2′-methoxyacetophenone (26 mg, 0.157 mmol) in absolute methanol (1.5 mL) was stirred at room temperature for 15 min. To the resulting mixture was added a solution of 2-(trifluoromethyl)-3-pyridinecarboxaldehyde (6a, 28 mg, 0.16 mmol) in absolute methanol (15 mL). The reaction was stirred overnight at room temperature (approx. 18 h). The reaction was then concentrated on a rotary evaporator and the resulting oily residue purified by chromatography on silica gel using a gradient of 0-100% ethyl acetate in hexane to provide the desired product (17 mg, 35%) as a light yellow waxy solid. Prepared using the general method from lithium hydroxide (1.2 mg, 0.01 mmol), 2′-methoxyacetophenone (72 mg, 0.48 mmol) and 3-trifluoromethyl-2-pyridinecarboxaldehyde (6d, 85 mg, 0.49 mmol) in absolute methanol (final reaction volume = 4 mL). The reaction mixture was purified by chromatography on silica gel (gradient of 0-100% ethyl acetate in hexane) to give the desired product as a yellow oil that hardened upon standing (77 mg, 54%). 1H NMR (CDCl3) delta 8.82 (d, J = 4.3 Hz 1H), 8.12 (d, J = 15.0 Hz, 1H), 8.01 (dd, J = 8.0, 1.6 Hz, 1H), 7.93 (dd, J = 15.0, 1.9 Hz, 1H), 7.70 (dd, J = 7.6, 1.8 Hz, 1H), 7.51 (t, J = 7.4 Hz, 1H), 7.41 (dd, J = 7.5, 4.6 Hz, 1H), 7.07 (t, J = 7.5 Hz, 1H), 7.02 (d, J = 8.1 Hz, 1H), 3.93 (s, 3H). 13C NMR (CDCl3) delta 192.4, 158.6, 152.3, 151.6, 135.4, 134.1, 133.9, 133.5, 130.6, 128.8, 125.8, 125.1, 123.2, 120.8, 111.6, 55.7. HRMS (FAB): calcd C16H12F3NO2 + H = 308.0898, found 308.0897.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Lounsbury, Nicole; Mateo, George; Jones, Brielle; Papaiahgari, Srinivas; Thimmulappa, Rajash K.; Teijaro, Christiana; Gordon, John; Korzekwa, Kenneth; Ye, Min; Allaway, Graham; Abou-Gharbia, Magid; Biswal, Shyam; Childers, Wayne; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5352 – 5359;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060814-36-9 ,Some common heterocyclic compound, 1060814-36-9, molecular formula is C15H21NO5, 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 C: Ethyl 4,5,6,7-tetrahydrofuro[3,2-c]pyridine-2-carboxylateTo a solution of 5-tert-Butyl 2-ethyl 6,7-dihydrofuro[3,2-c]pyridine-2,5(4H)- dicarboxylate (0.5g, 1.7 mmol) in DCM was added trifluoroacetic acid (TFA) (0.13 mL, 1.7 mmol) at 0-5 C. After the completion of addition, the reaction mixture was allowed to stir for 6 hours. The excess solvent and reagents were evaporated under reduced pressure. The crude product was triturated with hexane to afford the title compound as TFA salt (0.5 g, Yield 95 %). 1H NMR (DMSO-d6) 5(ppm): 1.36 (3Eta, t, – CH3), 2.77 (2H, brs, -CH2), 3.74 (2H, brs, -CH2), 4.32-4.38 (4H, m, -CH2), 5.02 (1H, brs, -NH), 7.02 (1H, s, Ar-H); MS m/z: 196.1 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060814-36-9, its application will become more common.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD; RAJAGOPAL, Sridharan; KILAMBI, Narasimhan; KACHHADIA, Virendra; RATHINASAMY, Suresh; BALASUBRAMANIAN, Gopalan; MANI, Umamaheswari; RAJAGOPALAN, Nirmala; PUSHPARAJ, Judy Auxcilia; ROY, Anshu Mittal; VISHWAKARMA, Lolaknath Santosh; NARAYANAN, Shridhar; KALIYAMOORTHY, Vadivel; THANASEKARAN, Ponpandian; THATAVARTHY KRISHNA, Rama; KANNAN, Kalaivani; KULATHINGAL, Jayanarayan; MOOKKAN, Jeyamurugan; CHIDAMBARAM VENKATESWARAN, Srinivasan; AHAMED ALI, Fakrudeen; WO2012/117421; (2012); 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. 17117-13-4, name is 2-Bromo-4-ethoxypyridine. A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Under an argon atmosphere, 0.81 g (4.00 mmol) of 2-bromo-4-ethoxy-pyridine, 1.02 g (6.40 mmol) of 2,6-difluoro-pyridyl-3-boronic acid, 0.0374 g (0.032 mmol) of Pd(PPh3)4 were dissolved in 30 mL of dioxane, followed by addition of 10 mL of an aqueous solution of 5wt% K2CO3, heated to reflux, stirred for 18 h. After naturally cooled to room temperature, an appropriate amount of distilled water was added, and the solution was extracted several times with ethyl acetate, the organic phase were combined and dried over anhydrous MgSO4. After filtration, solvent was removed from the filtrate under reduced pressure to give the crude product. The crude product was purified to silica gel column chromatography using a mixture of ethyl acetate and n-hexane (v/v=1:4) as eluent to obtain 0.56g of a colorless solid product in 59.6% yield. 1H NMR (400 MHz, CDCl3, ppm): delta 8.92 (d, 1H), 8.65 (d, 1H), 7.75 (d, 1H), 7.43 d, 1H), 6.92 (s, 1H), 4.12 (m, 2H), 1.90 (m, 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, 17117-13-4, 2-Bromo-4-ethoxypyridine.

Reference:
Patent; Ocean’s King Lighting Science & Technology Co., Ltd.; ZHOU, Mingjie; WANG, Ping; ZHANG, Juanjuan; ZHANG, Zhenhua; EP2727928; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2 ,Some common heterocyclic compound, 64951-08-2, molecular formula is C8H6N2O2, 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 l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), imidazo[l,2-a]pyridine-2- carboxylic acid (34 mg, 0.21 mmol) and EDCI.HC1 (41 mg, 0.21 mmol) in pyridine (2 mL) was stirred at 50 C for 2 h. The reaction mixture turned into white suspension from yellow solution. LCMS (Rt = 0.750 min; MS Calcd: 531.2; MS Found: 532.1 [M+H]+). The reaction mixture was diluted with water (25 mL), and then extracted with EtOAc/THF (25 mL x3, 1/1). The combined organic layer was washed with saturated aqueous NaHCCh (25 mL), brine (25 mL), dried over anhydrous Na2S04 and concentrated. The residue was triturated with MeCN (10 mL), then further purified by prep-HPLC (0.225% FA as an additive). Most of the MeCN was removed under reduced pressure and the remaining part was lyophilized to give N-(5-((5- methyl-8-(2-oxopyrrolidin-l-yl)-5H-chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3- yl)imidazo[l,2-a]pyridine-2-carboxamide (29.8 mg, yield: 40%) as ayellow solid. (1680) NMR (400 MHz, DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.01-2.11 (2H, m), 2.52-2.54 (2H, m), 3.85 (2H, t, J= 7.9 Hz), 5.29 (1H, q, J= 6.4 Hz), 6.79 (1H, s), 7.05 (1H, td, J= 6.8, 1.1 Hz), 7.33 (1H, dd, J= 8.7, 2.1 Hz), 7.39-7.44 (2H, m), 7.69 (1H, dd, J= 9.2, 0.9 Hz), 7.90 (1H, d, J= 8.8 Hz), 8.58 (1H, s), 8.59 (1H, t, J= 2.3 Hz), 8.65 (1H, td, J= 6.8, 1.1 Hz), 8.69 (1H, d, J= 2.3 Hz), 8.70 (1H, s), 8.78 (1H, t, J= 2.3 Hz), 9.52 (1H, brs), 10.51 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem