Pyridine-derivatives

Application of 877060-48-5 , The common heterocyclic compound, 877060-48-5, name is tert-Butyl 3-iodo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, molecular formula is C12H13IN2O2, 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.

1.1 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II)chloride and 15 mg (0.08 mmol) of copper(I)iodide are added to a solution, kept under nitrogen, of 1.37 g (4.00 mmol) of tert-butyl 3-iodopyrrolo[3,2-c]pyridine-1-carboxylate (prepared by the method of M. Lefoix et al, Synthesis, 2005, 20, 3581-3588) in 20 ml of tetrahydrofuran. Carbon monoxide is passed into this solution in an autoclave apparatus, and the mixture is stirred at a pressure of about 5 bar for 50 minutes. The apparatus is decompressed, 589 mg (6.00 mmol) of trimethylsilylacetylene and 405 mg (4.00 mmol) of triethylamine are added under nitrogen. The apparatus is re-pressurised to 5.8 bar with carbon monoxide, and the reaction mixture is stirred at room temperature for 45 hours. Saturated sodium chloride solution is added to the reaction mixture, which is then extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent: tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate as yellowish crystals; ESI 343.1.2 104 mg (0.75 mmol) of potassium carbonate are added to a solution of 103 mg (0.30 mmol of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate and 148 mg (0.75 mmol) of phenylguanidine carbonate in 1.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 68 hours. After cooling, 10 ml of water are added, and the mixture is stirred at 40 C. for 1 h. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving phenyl-[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]amine (?A1?) as pale-brown solid; ESI 287;1H NMR (DMSO-d6) delta [ppm] 6.90 (t, J=7.5 Hz, 1H), 7.25 (m, 3H), 7.39 (d, J=5.5 Hz, 1H), 7.76 (d, J=7.5 Hz, 2H), 8.22 (d, J=5.5 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.35 (s, 1H), 9.46 (s, 1H), 9.81 (s, 1H), 12.0 (bs, 1H).

The synthetic route of 877060-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/92527; (2011); 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.561297-96-9, name is 2-(Aminomethyl)-5-fluoropyridine, molecular formula is C6H7FN2, molecular weight is 126.1316, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-( -methylmethyl sulfonamido)benzofuran-5-yl)-3-methoxypicolinic acid (50 mg, 0.09 mmol), (5-fluoropyridin-2- yl)methanamine (200 mg, 1.58 mmol) and Et3N (0.2 mL) in THF (50 mL) was added T3P (0.05 mL) dropwise at 0C and the mixture was stirred for 3 h. After being diluted with water and extracted with EtOAc, the combined organic phases were washed with brine, dried over Na2S04, filtered and evaporated. The residue was purified by prep-TLC (PE : EtOAc = 1 : 2) to give the pure product of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-( – methylmethylsulfonamido)benzofuran-5-yl)-N-((5-fluoropyridin-2-yl)methyl)-3- methoxypicolinamide (20 mg, yield: 30%). XH-NMR (CDC13, 400 MHz) delta 8.60 (t, J= 4.8 Hz, 1H), 8.36 (d, J= 2.4 Hz, 1H), 7.99 (s, 1H), 7.92-7.95 (m, 2H), 7.73 (d, J= 8.4 Hz, 1H), 7.58 (s, 1H), 7.48 (d, J= 8.8 Hz, 1H), 7.24-7.42 (m, 2H), 7.17-7.22 (m, 2H), 5.91 (d, J= 3.6 Hz, 1H), 4.73 (d, J= 5.6 Hz, 2H), 4.01 (s, 3H), 3.18 (s, 3H), 2.97 (d, J= 4.8 Hz, 3H), 2.78 (s, 3H). MS (M+H)+: 636.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,561297-96-9, 2-(Aminomethyl)-5-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (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. 100-48-1, name is Isonicotinonitrile. A new synthetic method of this compound is introduced below., Recommanded Product: 100-48-1

General procedure: To a stirred mixture of nitrile (1.0 mmol) and thiosemicarbazide(1.1 mmol) was added trifluoroacetic acid (4 mL) and then themixture was refluxed for 6 h under stirring. After completion ofreaction cooled to room temperature and diluted with aqueousammonia. The precipitated solid was filtered off, washed with hotwater and dried in air. The product 14a-f were used in the next stepwithout further purification. Spectral data of compounds such as 5-phenyl-1,3,4-thiadiazol-2-amine (14a) [63], 5-(p-tolyl)-1,3,4-thiadiazol-2-amine (14b) [63], 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine (14c) [64], 5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (14d) [63], 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine(14e) [63] and 5-(thiophen-2-yl)-1,3,4-thiadiazol-2-amine (14f)[63] were agreement with literature report.

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, 100-48-1, Isonicotinonitrile.

Reference:
Article; Sakthivel, Palaniappan; Ilangovan, Andivelu; Kaushik, Mahabir Prasad; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 302 – 318;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6443-85-2, 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. 6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile. A new synthetic method of this compound is introduced below.

54.1.1 Synthesis of 3-cyano-3-(pyridin-3-yl)-pentanedioic acid diethyl ester Prepare by the method of example 1.1.2 using pyridin-3-yl-acetonitrile (0.161 mol) and ethyl bromoacetate (0.325 mol). Chromatograph on silica gel to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6443-85-2, 2-(Pyridin-3-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Hoechst Marion Roussel Inc.; US5824690; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 609-71-2, 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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C6H5NO3, 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.

(d) 5- Bromo-2-hydroxy-nicotinic acid To a suspension of 5.0 g (35.9 mmol) of 2-hydroxy-nicotinic acid in 30 ml acetic acid was added dropwise 7.5 g (46.7 mmol) bromine. The mixture was maintained at 70-80 C. overnight. The mixture was cooled and the acetic acid was removed under reduced pressure. Water (100 ml) was added and the product was filtered and washed with water (3*100 ml). The solid was dried in a vacuum oven at 65 C. for 48 hours to provide 6.1 g (78% yield) of the title compound. MS: m/z (APCI, AP+) 219.0 [M¡¤]+. CHN Analysis: Calcd: C, 33.06; H, 1.85; N, 6.42. Found: C, 32.91; H, 1.78; N, 6.23.

According to the analysis of related databases, 609-71-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Barvian, Nicole Chantel; Connor, David Thomas; O’Brien, Patrick Michael; Ortwine, Daniel Fred; Patt, William Chester; Shuler, Kevon Ray; Wilson, Michael William; US2002/161000; (2002); 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.53939-30-3, name is 5-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.44, as common compound, the synthetic route is as follows.HPLC of Formula: C5H3BrClN

EXAMPLE 13-(2-Methoxyphenyl)-6-(4-methoxyphenyl)-[l,2,4]triazolo[4,3-a]pyridine a) 5-Bromo-2-hydrazinylpyridine. A mixture of 5-bromo-2-chloropyridine (11.5 g, 60 mmol) and hydrazine hydrate (100 mL) was refluxed under Argon for 2 h. The mixture was cooled to room temperature, filtered and the solids were washed with water (50 mL x 3), dried to give the title compound (8.30 g, 74.4% yield) as yellow solids. MS: m/z 188.0 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53939-30-3, 5-Bromo-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; IMPACT THERAPEUTICS, INC.; DONG, Haijun; CAI, Suixiong; TIAN, Ye Edward; CHEN, Lei; YU, Zenghui; YIN, Feng; BI, Sheng; LIU, Lijun; WU, Lizhen; WO2012/65297; (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. 78790-79-1, name is 3-Amino-4-cyanopyridine, molecular formula is C6H5N3, 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. HPLC of Formula: C6H5N3

Example 10 4-Amino-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1,7-naphthyridin-2(1H)-one LiHMDS (3.6 eq) was added to ethyl [5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetate (1.0 eq) and 3-aminopyridine-4-carbonitrile (1.0 eq) in THF at 0 C. The reaction was stirred overnight. The resulting mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a green solid. The crude material was washed successively with CH2Cl2 and MeOH and then was purified by reverse phase HPLC to provide the desired product. LC/MS m/z 376.3 (MH+), Rt 1.70 minutes.

With the rapid development of chemical substances, we look forward to future research findings about 78790-79-1.

Reference:
Patent; Renhowe, Paul A.; Machajewski, Timothy; Shafer, Cynthia M.; Wernette-Hammond, Mary Ellen; Pecchi, Sabina; US2002/103230; (2002); 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.4548-45-2, name is 2-Chloro-5-nitropyridine, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of 2-chloro-5-nitropyridine (LXV) (2.0 g, 12.6 mmol) in EtOH (20 mL) was added tert-butyl piperazine-l-carboxylate (XCVI) (7.05 g, 37.9 mmol). The reaction was headed at 70C for 16 h. The reaction was concentrated under vacuum and then dissolved in EtOAc. The EtOAc was washed with 1 M NaOH, brine and then dried over MgS04 to give tert-butyl 4-(5-nitropyridin-2-yl)piperazine-l- carboxylate (XCVII) as a yellow solid (4.94 g). ESIMS found for C14H20N4O4 mlz 309.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4548-45-2, 2-Chloro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; HOOD, John; KC, Sunil Kumar; WO2013/40215; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 766-11-0 , The common heterocyclic compound, 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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 stirred solution of 5-bromo-2-fluoro-pyridine (10.0 g, 56.82 mmol) in ethanol (120 mL) was added hydrazine hydrate (11.38 g, 227 mmol) and heated to 80 C for 12 hours The reaction mixture was cooled to room temperature and treated with ice water (200 mL). The precipitated solid was filtered, washed with water and dried to get the product (10.7 g) as a solid. It was used for the next step without further purification.

The synthetic route of 766-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); 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. 131747-63-2, name is 4-Bromopicolinaldehyde. A new synthetic method of this compound is introduced below., Safety of 4-Bromopicolinaldehyde

Example 30i 4-Bromo-2-(difluoromethyl)pyridine Diethylaminosulphur trifluoride (4.08 mL, 33.31 mmol) was added to 4-bromopicolinaldehyde (0.267 M in chloroform) (100 mL, 26.7 mmol) at 0 C. under an atmosphere of argon. The reaction mixture was stirred over night while the temperature was raised to room temperature. The reaction was quenched by addition of aqueous sodium bicarbonate (sat.) and was further diluted with dichloromethane. The solids were filtered off through a pad of Celite. The organic layer was collected and the water phase was extracted with dichloromethane (*3). The organic layers were pooled, dried (Na2SO4), filtered and concentrated. Purification by silica chromatography using 0 to 60% diethyl ether in pentane gave the title compound (1.78 g, 32%). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.59 (d, 1H) 7.98 (d, 1H) 7.90 (dt, 1H) 6.98 (t, 1 H); MS (APCI+) m/z 208, 210 [M+H]+.

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, 131747-63-2, 4-Bromopicolinaldehyde.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem