Pyridine-derivatives

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. 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-iodo-3-methylpyridine

N-((S)-1-(4-((R)-1-(2-Chloro-3-methylpyridin-4-yl)pyrrolidin-3-yloxy)phenyl)ethyl)acetamide Under inert gas atmosphere 0.80 g (2.53 mmol) of example XIII.1, 0.65 g (2.53 mmol) of 2-chloro-4-iodo-3-methyl-pyridine, 1.00 g (10.4 mmol) NaOtBu and 100 mg (0.14 mmol) chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)(2-(2-aminoethyl)-phenyl)-palladium (II) are added to 50 mL dioxane and stirred at 45 C. over night. Afterwards the solvent is removed, water is added and the product is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (ACN/H2O/TFA). C20H24ClN3O2 (M=373.9 g/mol) ESI-MS: 374 [M+H]+Rt(HPLC):0.77 min (method M)

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, 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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 100 mL round-bottom flask was charged with NiCl2*6H2O (40 mg, 0.15 mmol) and DMF (10 mL). The resulting solution was stirred and heated to 40 C. Then, 2-chloro-5-methoxypyridine (6,3 mmol), anhydrous LiCl (130 mg, 3 mmol), and zinc dust (230 mg,3.6 mmol) were added. When the temperature rose to 50 C, a grain of iodine crystal and two drops of acetic acid were added to the mixture. The mixture was stirred at 55-60 C until complete conversion of 2-halopyridine (monitored by TLC). To the cooled reaction mixture was added 1 N HCl aqueous solution (5 mL) to consume the remaining zinc dust. The resulting mixture was made alkaline with aqueous ammonia (25%) and diluted with CH2Cl2. The organic layers were collected, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel (Hexane/EtOAc 10:1, v/v) to afford desired 5,5′-dimethoxy-2,2′-bipyridine as a light yellow solid, 130 mg, 40% yield. 1H NMR (500 MHz, CDCl3): d 8.33 (d, J 3.0 Hz, 2H, ArH), 8.24 (d, J 9.0 Hz,2H, ArH), 7.30 (dd, J1 9.0 Hz and J2 3.0 Hz, 2H, ArH), 3.91 (s, 6H,2OCH3).

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 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Article; Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; 29; (2017); p. 4150 – 4159;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 947249-13-0, 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. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 13.39 mmol) in 1 ,4-dioxane (60 mL) were added4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1 ,3,2-dioxaborolane) (3.74 g, 14.73 mmol),tricyclohexylphosphine (525 mg, 1.87 mmol), potassium acetate (3.28 g, 33.47 mmol) and tris(dibenzylideneacetone)dipalladium(0) (490 mg, 0.53 mmol). The reaction mixture was purged with nitrogen for 2 mm and heated to 110 C for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were dried over sodium sulfate andconcentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25% ethyl acetate in hexane) affording 3-(difluoromethoxy)-5- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine (1.3 g, 34%): 1H NMR (400 MHz, DMSO-d6) oe: 8.03 (s, 1H), 7.33 (s, 1H), 7.11 (t, I = 73.6 Hz, 1H),6.44 (s, 2H), 1.25 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866807-27-4, Adding some certain compound to certain chemical reactions, such as: 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid,molecular formula is C6H5ClN2O2, 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 866807-27-4.

Step 4: Preperation of 3-amino-6-chloro-pyridine-2- carboxylic acid methyl ester; 3-Amino-6-chloro-pyridine-2-carboxylic acid (636 mg) was suspended in methanol (8 mL) and toluene (22 mL) was added. A solution of (trimethylsilyl) diazomethane (2.0 M in hexane,2.4 mL) was added slowly to the reaction mixture. After 1 hour stirring at room temperature, another portion of(trimethylsilyl) diazomethane (550 mul) was added and the mixture was stirred for additional 45 minutes. The reaction mixture was quenched with water and extracted 3x with ethyl acetate. The combined organic layer was washed with 2N hydrochloric acid, saturated bicarbonate solution and brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, choroform/ethyl acetate = 50:1, Rf = 0.30) to afford 365 mg of the title compound of the formulaas a yellow solid. The compound still contained -30% of an unknown impurity and was used in the next step without further purification.1H-NMR (CDCl3, TMS) delta (ppm) : 3.96 (3H, s) , 5.82 (2H, br s), 7.05 (IH, d, J = 9 Hz), 7.23 (IH, d, J = 9 Hz).

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. 866807-27-4, 3-Amino-6-chloropyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 197376-47-9, 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 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl (6-chloropyridin-3-yl)acetate (8.2 g) in N,N-dimethylformamide (50 mL) was added sodium hydride (60% in mineral oil, 2.4 g) under ice-cooling, and the mixture was stirred for 30 min. To the reaction mixture was added methyl iodide (7.7 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added methyl iodide (3.8 mL), and the mixture was stirred at 40 C. for 15 hr. The reaction mixture was cooled to 0 C., N,N-dimethylformamide (15 mL) and sodium hydride (60% in mineral oil, 1.2 g) were added thereto, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added methyl iodide (2.5 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (4.4 g). (1557) MS(ESI+): [M+H]+ 227.8

According to the analysis of related databases, 197376-47-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1092286-30-0, 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 1092286-30-0 as follows.

A mixture of 4-(6-(4-amino-4-methylpiperidin-l-yl)pyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile dihydrochloride (Intermediate P48;53 mg, 0.107 mmol), HATU (44.9mg, 0.118 mmol), and 5-Chloro-2-methyl-3- pyridinecarboxylic acid (36.9 mg, 0.107 mmol) in DMSO (1.28 mL, 0.1 M) was treated with DIEA (0.09 mL, 0.54 mmol) and then stirred for 18 h at ambient temperature. The reaction mixture was diluted with EtOAc and washed with water. The organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo. The residue was suspended in 60:40 ACN:water containing 2% TFA. The solution was purified directly by C18 reverse phase chromatography (5-95% ACN in water with 0.1% TFA as the gradient eluent) to afford the title compound as the TFA salt. The TFA salt was treated with saturated NaHCCb(aq) and extracted with DCM. The combined organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo to afford the title compound (26.1 mg, 42% yield). MS (apci) m/z = 574.2 (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,1092286-30-0, its application will become more common.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-55-2 ,Some common heterocyclic compound, 131747-55-2, molecular formula is C6H6FNO, 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.

Di-tert-butyl azodicarboxylate (0.36 g, 1.57 mmol) was added to a suspension of (2-fluoropyridin-3-yl)methanol (10, 0.20 g, 1.57 mmol), N-(4-(2,4-difluorophenoxy)phenyl)-N-ethylsulfonylamine (0.49 g, 1.56 mmol) and polystyrene resin-bound triphenylphosphine (0.52 g, 1.57 mmol, 3 mmol/g) in anhydrous tetrahydrofuran (5 mL) at 0 C. under nitrogen. The resulting yellow suspension was warmed to room temperature and stirred for 19 h, after which additional polystyrene resin bound triphenylphosphine (0.52 g, 1.57 mmol, 3 mmol/g) and di-tert-butyl azodicarboxylate (0.36 g, 1.57 mmol) were added. This solution was stirred for 24 h after which the suspension was diluted with anhydrous tetrahydrofuran (100 mL) and the solids were removed by vacuum filtration. The filtrate solvent was removed under reduced pressure to provide the crude product as a yellow oil. This oil was purified by medium pressure liquid chromatography on silica gel, eluting with hexanes/ethyl acetate (7:3), to provide a colorless oil. This oil was triturated with hexanes/ethyl acetate (4-5 mL) to give the title compound as a white powder (0.28 g, 53%): mp 110-112 C.; TLC Rf (3:2 hexanes/ethyl acetate)=0.44; 1H NMR (300 MHz) 8.11 (m, 1H), 7.90 (m, 1H), 7.24-7.15 (m, 3H), 7.11-7.03 (m, 1H), 6.98-6.86 (m, 2H), 6.84 (d, J=6.8 Hz, 2H), 4.91 (s, 2H), 3.15-3.07 (q, J=7.4 Hz, 2H), 1.43 (t, J 5=7.4 Hz, 1H) ppm; 13C NMR (75 MHz) 163.3, 161.3, 160.1, 157.8, 156.5, 153.1, 147.5 (d, J=14.9 Hz), 141.7, 139.1, 133.6, 130.5, 123.8 (d, J=9.7 Hz), 122.1, 119.1 (d, J=29.2 Hz), 117.5, 112.0 (d, J=22.9 Hz), 106.0 (t, J=24.3 Hz), 49.1, 46.0, 8.44 ppm; APCI MS m/z 423 [C20H17F3N2O3S+H]+. Anal. Calcd. for C20H17F3N2O3S: C, 56.87; H, 4.06; N, 6.63. Found: C, 56.90; H, 4.10; N, 6.45.

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. 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Coleman, Darrell Stephen; Jagdmann, Gunnar Erik; Johnson, Kirk Willis; Johnson, Michael Parvin; Large, Thomas Hallett; Monn, James Allen; Schoepp, Darryle Darwin; Barda, David Anthony; Britton, Thomas Charles; Dressman, Bruce Anthony; Henry, Steven Scott; Hornback, William Joseph; Tizzano, Joseph Patrick; Fichtner, Michael William; US2004/6114; (2004); 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. 588720-29-0, name is Imidazo[1,5-a]pyridine-7-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 588720-29-0

To a 50 mL single neck RB flask starting 1H-Imidazol (1,5-a)pyridine-7-carboxylic acid (0.5 g, 3.086 mmol) was added, followed by ethyl ester of L-Leucine Hydrochloride (0.5 g, 3.086 mmol), HATU (0.323 g, 0.85 mmol) and DMF (8 mL). The contents were stirred for 5 mins. After clear solution formation DIPEA (1.1 mL, 6.172 mmol) was added and the reaction mass stirred for 16h at 20-30C. After 16h, the completion of the reaction was confirmed byTLC/LCMS, and worked-up. Ice-cold water (2OmL) was added slowly to the reaction mixture with stirring. The product was extracted with ethyl acetate (2x2OmL). The ethyl acetate extracts were separated washed with (1×20 mL) water, separated the organics, dried over anhydrous sodium sulphate and distilled off the volatiles under reduced pressure to get the crude product. This crude material was subjected to purification using preparative RP HPLC. The pure material thus obtained yielded 60-70% yield of the product of desired purity.

The synthetic route of 588720-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALKEM LABORATORIES LTD.; NAGARAJ, Harish Kumar Mysore; BANDODKAR, Balachandra S; RAVILLA, Lokesh; YELLAPU, Sudhakar; RUDRESHA, Ashok Seegebagi; SINGH, Jitendra Kumar; G, Vaidyanathan.; (95 pag.)WO2016/27285; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88912-24-7 ,Some common heterocyclic compound, 88912-24-7, molecular formula is C6H3Cl2NO2, 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.

EXAMPLE 12 2,3-bis(methylthio)pyridine In a 4-necked flask equipped with a Dry Ice condenser, mechanical stirrer, thermometer and dropping funnel, 172.2 g of t-BuOK was dissolved in 200 ml of DMSO at room temperature with stirring under N2. The solution was cooled with an ice bath while 50.0 g of methanethiol was added. The mixture was stirred for 30 minutes, then the ice bath was removed. A solution of 5,6-dichloro-2-pyridinecarboxylic acid (90.6 g) in 250 ml of DMSO was added at a rate such that the exotherm did not cause the temperature of the mixture to exceed 75 C. A dense slurry formed. An additional 500 ml of DMSO was added, and the slurry was stirred for 42 hours at 60 C. After cooling to room temperature, 500 ml of water was added to the reaction mixture, which was then added to 3.5 liters of ice water, and acidified to pH 1 with concentrated HCl. The yellow precipitate which formed was collected and dried which gave 87.33 g of a mixture of 5-chloro-6-(methylthio)-2-pyridinecarboxylic acid (~3.36 g) and 5,6-bis(methylthio)-2-pyridinecarboxylic acid (~83.97 g). The relative amounts of the 5-chloro-6-(methylthio)-2-pyridinecarboxylic acid and 5,6-bis(methylthio)-2-pyridinecarboxylic acid were estimated based on the amounts of the mono and bis-adducts isolated after decarboxylation.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88912-24-7, its application will become more common.

Reference:
Patent; The Dow Chemical Company; US4616087; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, 1026796-81-5, blongs to pyridine-derivatives compound. COA of Formula: C7H7BrN2O

[00348] To a solution of N-(4-bromopyridin-2-yl)acetamide (350 mg, 1.6 mmol) in DCM (20 niL) was added mCPBA (1.26 g, 7.3 mmol) at 0C. The reaction mixture was allowed to stir at ii for 3 h. The reaction mixture was then diluted with water and saturated K2C03 solution, and extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to provide N-(4-bromo-1-oxidopyridin-2- yl)acetamide (340 mg, 90%). LCMS (FA): m/z 231.3 (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,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; WONG, Tzu-Tshin; XU, He; XU, Tianlin; YE, Yingchun; WO2015/108861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem