Category: pyridine-derivatives

Electric Literature of 272-23-1, Adding some certain compound to certain chemical reactions, such as: 272-23-1, name is Thieno[2,3-b]pyridine,molecular formula is C7H5NS, 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 272-23-1.

Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N?,N?-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66%) of brown solid; m.p. 131.5-132.5 C. Recrystallizations from ethanol (once with charcoal) gave white needles. 1H NMR (300 MHz, CDCl3) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl3, cm-1) 1682 (C=O). MS (EI, 70 eV): m/z [%] = 162[M]+ (100), 134[M-CO]+ (26). HRMS (FAB+) calculated for C8H6NOS [M+1] 164.0170, found 164.0167.

According to the analysis of related databases, 272-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60154-05-4, 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. 60154-05-4, name is 5-Iodo-1-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

2,2-Dimethyl-3-(3-{(S)-1-[4-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-ethyl}-2-oxo-(S)-6-phenyl-[1,3]oxazinan-6-yl)-propionitrile was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one following procedures analogous to those described Example 71 Method 2 to prepare 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile. (S)-6-(2-hydroxy-2-methyl-propyl)-3-{(S)-1-[4-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one, is obtained from coupling (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one with 5-iodo-1-methyl-1H-pyridin-2-one by the action of Pd(PPh3)4 and 2 M aqueous Na2CO3 solution in a mixture of methanol and dioxane (1:3) at 80 C. The compound that had been obtained as a foam was dissolved in a small amount of ethyl acetate and stirred overnight at rt. The solid was filtered by suction, washed with a small amount of diethylether and dried. Melting point: 143-145 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide, molecular formula is C6H7N3O, 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 solution of 5-aminopyridine-2-carboxamide (248.6 mg, 1.813 mmol) in dichloromethane (2.50 mL) and N,N-diisopropylethylamine (420 mu, 2.41 mmol) was cooled to 0 C. A solution of ice cold 2-fluoro-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoyl chloride in dichloromethane (2.5 inL) was added slowly dropwise to the stirring amine solution. The mixture was removed from the ice bath after 1 hour and stirred at RT for 69 hours. The reaction was diluted with dichloromethane and washed with water, 1 N HCl, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2S04, filtered and the solvent was evaporated under reduced pressure. The crude material was purified by silica gel chromatography (ethyl acetate/hexane gradient) to yield 5 – [[2-fluoro-6- [2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy] -3 – (trifluoromethyl)benzoyl]amino]pyridine-2-carboxamide (326 mg, 51%) as a white solid. ESI-MS m/z calc. 536.10, found 537.0 (M+l)+; retention time (Method C): 2.48 minutes (5 minute run). ‘H NMR (400 MHz, DMSO-d6) delta 11.36 (s, 1H), 8.88 (d, J = 2.5 Hz, 1H), 8.31 (dd, J = 8.6, 2.5 Hz, 1H), 8.07 (d, J = 8.6 Hz, 1H), 8.03 (d, J = 2.8 Hz, 1H), 7.81 (t, J = 8.6 Hz, 1H), 7.57 (d, J = 2.8 Hz, 1H), 7.37 (d, J = 8.7 Hz, 1H), 7.25 (d, J = 2.8 Hz, 1H), 7.12 – 6.92 (m, 1H), 6.69 (d, J = 8.9 Hz, 1H) ppm.

According to the analysis of related databases, 145255-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (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. 84539-34-4, name is 4-Amino-3,5-dibromopyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 84539-34-4

Intermediate s:3-bromo-5-{cyclohex-1-en-1-yl)pyridln-4-amine To a stirred and nitrogen degassed solution of 3,5-dibromopyridin-4-amine (CAS 84539-34-4; 2.00 g, 7.94 mmol), potassium carbonate (2.20 g, 15.88 mmol) and (cyclohex-i-en-i-yl)boronic acid (CM 89490-05-1; 1.10 g, 8.73 mmol) in dioxane (26 mL) and water (1.6 mL) was added bis(triphenylphosphine)palladium(1I) dichioride (CAS 13965-03-2; 557 mg, 794 iimol). The reaction mixture was heated under microwave irradiation at 130 C for 1.5 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organics were dried (MgSOJ, filtered and concentrated in vczczw. The crude product was purified by column chromatography (silica, 0-50% EtOAc / petroleum ether) to afford the title compound.?H NMR (400 MHz, DK{SO-d5) 6 ppm i.8 – 1.69 (m, 2 H) 1.69 – 1.78 (m, 2 H) 2.15 (br. S., 4 H) 5.62 – (m, H) 7.78 (s, i H) 8.i6 (s, iH)MS ES: 255

The synthetic route of 84539-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 934279-60-4, 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. 934279-60-4, name is 2-Chloro-5-(trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of crude 2-chloro-5-trifluoromethylpyridine-3-carbardehyde in ethanol (60 ml_), sodium tetraborohydride (2.90 g, 0.077 mol) is added portionwise and stirred for 30 min at room temperature. After adding sat. ammonium chloride solution, the mixture is extracted with ethyl acetate. The organic layer is washed with sat. ammonium chloride solution, brine, dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel column chromatography to give 2-chloro-5-trifluoromethylpyridin-3-ylmethanol (12.3 g, 76 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934279-60-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75291-85-9 ,Some common heterocyclic compound, 75291-85-9, molecular formula is C6H4BrClN2O, 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.

Preparation 119tert-butyl (3R,4S)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate A solution of 5-bromo-2-chloronicotinamide (Preparation 177, 11.7 g, 49.8 mmol), tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1 -carboxylate (WO 20131011402 Al, 10.9 g, 49.8 mmol) and potassium tert-butoxide (6.72 g, 60 mmol) in DMSO (165 mL) was stirred at roomtemperature for 16 hours. The reaction was quenched by the addition of water (500 mL) and extracted into EtOAc (3 x 500 mL). The organic layers were combined, concentrated in vacuo and the residue triturated with diethylether to afford the title compound as a pale yellow powder(17.8 g, 85%).1H NMR (400 MHz, DMSO-d6): O ppm 1.39 (5, 9H), 1.82 (m, 1H), 1.94 (m, 1H), 3.01 (m, 1H),3.27 (m, 1H), 3.93 (5, 1H), 4.14 (5, 1H), 4.98 (d, 1H), 5.38 (dddd, 1H), 7.51 (5, 1H), 7.90 (5, 1H),8.26 (d, 1H), 8.41 (d, 1H). MS mlz 418 [M79Br-fH]

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. 75291-85-9, 5-Bromo-2-chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1026796-81-5 , The common heterocyclic compound, 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, 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 2: N-[4-(trimethylstannyl)pyridin-2-yl]acetamide Intermediate 20 A mixture of N-(4-bromopyridin-2-yl)acetamide (12.6 g, 58.7 mmol), hexamethylditin (25 g, 76.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.39 g, 2.93 mmol) in 1,4-dioxane (300 mL) was heated at 95 C. for 3 h. The solvents were removed under reduced pressure. DCM was added and the resulting black precipitate was removed by filtration and washed with DCM. The filtrate was evaporated. The residue was purified by silica gel chromatography (25-40% EtOAc/hexanes) to afford N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (12.6 g, 72%). 1H NMR (400 MHz, CDCl3) delta ppm 8.33 (s, 1H), 8.22 (s, 1H), 8.17 (dd, J=4.7, 0.9 Hz, 1H), 7.14 (dd, J=4.7, 0.6 Hz, 1H), 2.20 (s, 3H), 0.34 (s, 9H).

The synthetic route of 1026796-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmacuticals, Inc.; US2012/15943; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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.

2,6-Dibromo-4-methylpyridine (3.76 g, 14.98 mmol) in dichloromethane (DCM) (80 mL) was added.Cool to -78 C. under nitrogen.While maintaining the internal temperature below -70 C,n-Butyllithium (2.5 M in hexane) (6.59 mL, 16.48 mmol) was added dropwise.After the addition is completeThe solution becomes a suspensionStir at -78 C. for 15 minutes.While keeping the internal temperature below -60 C,A solution of dihydrofuran-3 (2H) -one (1.548 g, 17.98 mmol) in 2 mL of DCM was added over 3 minutes.After the addition is completeReduce the temperature back to -78 C,Stir for 30 minutes.The product with saturated aqueous NH4Cl,Extracted with DCM.The organic portion was dried over MgSO 4, filtered and concentrated to give a residue that was purified on a silica gel column eluted with 0-50% ethyl acetate / heptane to give the product (2.13 g, yield). 55%).

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-25-1 ,Some common heterocyclic compound, 133081-25-1, molecular formula is C11H15N3O4, 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 2-chloro-4,6-dimethyl-1,3,5-triazine (CDMT) (1.76 g, 10 mmol), 2 (2.53 g, 10 mmol) in THF (10 ml), and N-methylmorpholine (1.1 ml, 10 mmol) and after 4 h 4b (2.83 g, 10 mmol) in THF were combined as above to afford 5b as yellow solid. Compound 5b: mp 188-190 C; yield 38%; IR (KBr) nu (cm-1): 1522.0, 1636.2, 1717.8, 2862.6, 2934.4, 3242.6; 1H NMR (CD3OD) (delta ppm): 8.4 (2H, d, J = 8.1 Hz, ArH), 7.7-7.9 (2H, m, ArH), 7.6 (1H, d, J = 5.8 Hz, CCHC), 7.5 (1H, t, J = 5.7 Hz, ArH), 6.6 (1H, d, J = 8.7 Hz, CCHC), 4.6 (2H, s, NH), 3.9-4.0 (2H, m, NHCH2), 3.7 (1H, m, NH), 3.3-3.4 (2H, m, CH2N), 3.0 (2H, m, CH2), 2.7 (2H, m, CH2), 2.5 (1H, m, NH), 1.8-2.0 (8H, m, CH2), 1.7 (2H, m, CH2), 1.4-1.5 (9H, m, BOC); MS (FAB) m/z (M + 1) 519.4, 419.3, 199.1; MS-HR (FAB) Calcd for C28H38N6O3: 518.30054. Found: 519.30688 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,133081-25-1, its application will become more common.

Reference:
Article; Szymanski, Pawel; Markowicz, Magdalena; Mikiciuk-Olasik, Elbieta; Bioorganic Chemistry; vol. 39; 4; (2011); p. 138 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1147422-00-1, 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. 1147422-00-1, name is tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate. A new synthetic method of this compound is introduced below.

5-(2-amino-4-(4-chlorothiophen-2-yl)thiazol-5-yl)-octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate (100mg, 0.4mmol), and 5-bromo-4-(4-chloro-thiophen-2-yl)-thiazole-2-amine (157mg, 0.5mmol) were added to N,N-dimethylformamide (4mL), and then triethylamine (447mg, 4.4mmol) was added. The mixture was warmed to 90C and reacted for 6 h. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic phases were combined and washed successively with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to produce a crude product. The crude product was purified with a silica gel column chromatography to produce the title compound as a yellow solid (170mg). ESI-MS (m/z): 441.2 [M + H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.; CAI, Jiaqiang; YU, Nan; ZENG, Hong; SONG, Hongmei; QING, Yan; SONG, Shuai; DENG, Hanwen; TANG, Zujian; DUAN, Xiaofan; HUANG, Haitao; YE, Hong; LIU, Gang; WANG, Lichun; WANG, Jingyi; (81 pag.)EP3511332; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem