Month: April 2022

Related Products of 138647-49-1, 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. 138647-49-1, name is tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl4-(((trifluoromethyl)sulfonyl)oxy)-3 ,6-dihydropyridine-1(2H)-carboxylate (5.6 g, 16.8 mmol), Et3N (4.7 ml, 33.0 mmol) in DMF (69 ml) andMeOH (52 ml) was added PPh3 (0.2 g, 1.0 mmol) and Pd(OAc)2 (0.1 g, 0.5 mmol) at RT under nitrogen followed by stirring under CO atmosphere for 12 h. The reaction mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography to give 2.0 g of the title compound as a greenish liquid. 1H-NMR (400MHz; DMSO-d6): oe 6.85 (d, 1H), 4.00 (t, 2H), 3.67 (s, 3H), 3.42 (d, 2H), 2.25 (t, 2H),1.41 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138647-49-1, tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; DIN BELLE, David; MAeKELAe, Mikko; PASSINIEMI, Mikko; PIETIKAeINEN, Pekka; RUMMAKKO, Petteri; TIAINEN, Eija; VAISMAA, Matti; WOHLFAHRT, Gerd; (254 pag.)WO2018/115591; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 36953-37-4, 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. 36953-37-4, name is 4-Bromopyridin-2(1H)-one, molecular formula is C5H4BrNO, 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.

To a solution of sodium 2-chloro-2,2-difluoroacetate (12.38 g, 81 mmol) in MeCN (400 mL) was added 4-bromopyridin-2(1H)-one (10.09 g, 58 mmol) and the reaction was refluxed for 20 h. The mixture was filtered and the solid purified by chromatography on silica gel (80 g column, 0-10% EtOAc/isohexane) to afford the title compound (6.75 g, 51%) as a clear colourless liquid.1H NMR (DMSO-d6) d 8.10 (d, J = 5.5 Hz, 1H), 7.86-7.52 (m, 2H), 7.49 (d, J = 1.6 Hz, 1H).

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 36953-37-4, 4-Bromopyridin-2(1H)-one.

Reference:
Patent; INFLAZOME LIMITED; MILLER, David; MACLEOD, Angus; THOM, Stephen; MCPHERSON, Christopher G.; ALANINE, Thomas; CARRILLO ARREGUI, Jokin; CIANA, Claire-Lise; SHANNON, Jonathan; VAN WILTENBURG, Jimmy; DEN HARTOG, Jacobus Antonius Joseph; (603 pag.)WO2019/211463; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1221171-70-5 ,Some common heterocyclic compound, 1221171-70-5, molecular formula is C6H3ClF3NO, 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 cooled solution of 2-chloro-6-(trifluoromethoxy)pyridine (0.3 g, 1.51 mmol) in anhydrous THF (2 ml.) was added LDA (2M in THF, 0.9 ml_, 1 .82 mmol) dropwise over 5 min and the resulting solution was stirred for 2 h at -78C. Iodine (0.5 g, 1 .97 mmol) in anhydrous TFIF (1 ml.) was then added dropwise over 5 min at -78C and stirred for an hour at same temperature. The reaction mixture was then quenched with saturated aq.NFUCI solution (5 ml_). Crude was extracted with EtOAc (10 mL X 2) and combined organic phases were washed with Na2S2C>3 (2M, 10 mL), dried over sodium sulphate, evaporated under reduced pressure to afford a title compound as colourless liquid (0.30g, 61 .07 %), Rf = 0.6 (05% EtOAc in n-Hexane); 1H NMR (300 MHz, Chloroform-d) d 8.09 (d, J = 8.0 Hz, 1 H), 7.02 (d, J = 8.2 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,1221171-70-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; NG, Shuyi Pearly; RAO, Srinivasa P S; (126 pag.)WO2019/244049; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1032943-43-3, 4-Bromo-1H-pyrazolo[3,4-c]pyridine, 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, Safety of 4-Bromo-1H-pyrazolo[3,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 4-Bromo-1H-pyrazolo[3,4-c]pyridine

To a stirred solution of 4-bromo-1H-pyrazolo[3,4-c]pyridine (0.320 g, 1.62 mmol) inDMF (10 mL)were addedZn(CN)2(0.190 g, 1.62 mmol) andZnCl2(0.110 g, 0.808 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes and tetrakis(triphenylphosphine)palladium(0) (0.373 g, 0.323 mmol) was added and again degassed with nitrogen for 5 minutes. The reaction mixture was heated in a sealed tube at100 C for 10 h. The reaction mixture was cooled and concentrated under reduced pressure, diluted with water (40 mL) and extracted with EtOAc (2 x 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by CombiFlash (Redisep-24 g, 70 % EtOAc/n-hexanes), to obtain Intermediate 1-10 (0.14 g, 60 %). ?HNIVIR (400 MHz, DMSO-d6) ppm 8.50 (s, 1 H), 8.75 (s, 1 H), 9.38 (s, 1 H), 14.32 (br, s,1 H). LCMS (methodE), retention time 0.647 mi [M+H] 145.0.

The synthetic route of 1032943-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; RICHTER, Jeremy; YADAV, Navnath Dnyanoba; PANDA, Manoranjan; GODESI, Sreenivasulu; (132 pag.)WO2017/184662; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65169-42-8 , The common heterocyclic compound, 65169-42-8, name is Methyl 6-chloro-5-methylnicotinate, molecular formula is C8H8ClNO2, 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 3; 5-Formyl-3-methyl-2-pyridinecarbonitrile (Used to prepare Example 32) (a) (6-Chloro-5-methyl-3-pyridinyl)methanolTo a solution of methyl 6-chloro-5-methyl-3-pyridinecarboxylate (84 mg, 0.453 mmol) in DCM (2 ml), DIBAL-H (1.5 M solution in toluene, 0.905 ml, 1.358 mmol) was added dropwise under N2 at -78 C. The reaction mixture was allowed to attain rt and stirred overnight. After 18 h, TLC showed no starting material. The reaction was quenched by addition of sodium-potassium tartrate saturated solution, extracted with DCM, dried, filtered, and concentrated to afford (6-chloro-5-methyl-3-pyridinyl)methanol (63 mg, 0.400 mmol, 88% yield) pure enough to be used in the next step.1H-NMR (delta ppm, CDCl3): 8.17 (s, 1H), 7.60 (s, 1H), 4.69 (s, 2H), 2.37 (s, 3H).

The synthetic route of 65169-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alemparte-Gallardo, Carlos; Barfoot, Christopher; Barros-Aguirre, David; Cacho-Izquierdo, Monica; Fiandor Roman, Jose Maria; Hennessy, Alan Joseph; Pearson, Neil David; Remuinan-Blanco, Modesto Jesus; US2009/306089; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, 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.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%).

According to the analysis of related databases, 915006-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 956010-87-0, 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 956010-87-0 as follows.

To compound 12 (100 mg, 0.53 mmol) and morpholine (93 mg, 1.07 mmol) was added a 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was extracted with ethyl acetate, neutralized with 4N HCl solution and again extracted. The combined organic layers were dried over sodium sulfate, and the solvent was evaporated to yield 117mg (95 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 3.63-3.75 (m, 6H), 4.07-4.15 (m, 2H), 7.32 (dd, J=8.1, 4.5Hz, 1H), 8.42 (dd, J=8.1, 1.5Hz, 1H), 8.60 (dd, J=4.5, 1.5Hz, 1H), 14.15 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 42.3, 46.9, 66.1, 66.4, 114.8, 118.2, 131.1, 138.1, 149.5, 151.6, 161.0. HRMS m/z calcd for C11H12N4O2: 232.0960; found: 232.0962.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
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.89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6INO

Preparation 94 To a suspension of 3-iodo-4-methoxypyridine (0.62g), 3-nitrophenylboronic acid (0.57g) and tetrakis(triphenylphosphine)palladium(0) (152mg) in dimetoxyethane (10ml) was added aqueous sodium carbonate (2M, 3.43ml) and the mixture was stirred at 60C for 6 hours. The mixture was diluted with ethyl acetate and washed with aqueous sodium hydroxide (1N) and brine. The separated organic layer was dried over magnesium sulfate and evaporated. The residue was purified with silica gel (25g) column chromatography and eluted with 40-80% ethyl acetate in n-hexane to give 3-(4-methoxypyridin-3-yl)nitrobenzene (84mg). APCI-mass;m/z231(M+H+) 1H-NMR(DMSO-d6): delta;3.90(3H,s), 7.24(1H,d,J=5.8Hz), 7.75(1H,t,J=8.0Hz), 8.00 (1H,d,J=8.0Hz), 8.24(1H,dt,J=8.2Hz,1.1Hz), 8.35(1H,t,J=1.0Hz), 8.48(1H,s), 8.53(1H, d,J=7.6Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89640-55-1, 3-Iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1264820; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3796-24-5, Adding some certain compound to certain chemical reactions, such as: 3796-24-5, name is 4-(Trifluoromethyl)pyridine,molecular formula is C6H4F3N, 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 3796-24-5.

Reagents and conditions: (i) mCPBA, EtOAc; (ii) POCl3; (iii) PdPPh3) 2C12, Ba(OH)2, DME-H2O, 110 0C; (iv) 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine, Pd(OAc)2, Xantphos, K2CO3, dioxane, 120 0C.[0054] Scheme III above shows a general synthetic route that is used for preparing the compounds III-5. Compounds of formula III-5 can be prepared from intermediate III-l. The formation of chloropyridine derivative III-2 is achieved by treating the corresponding pyridine III-l with m-CPBA in EtOAc followed by conversion of the corresponding N-oxide to the chloropyridine by treating it with POCl3. Intermediate III-2 is then reacted with the corresponding boronic acid derivative to yield compound III- 3 using Suzuki coupling conditions well known for those skilled in the art. This reaction is amenable to a variety of boronic acid derivatives. The pyridine III-3 is then converted in a chloropyridine derivative III-4 using the same two step procedures as used in step 1, m-CPBA oxidation followed by POCl3 treatment. Intermediate III-4 is then treated with 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine in the presence of Pd as a catalyst to yield the final compound III-5.

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. 3796-24-5, 4-(Trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, name: 5-Bromo-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. name: 5-Bromo-N2-methylpyridine-2,3-diamine

To a solution of 5-bromo-N2-methylpyridine-2,3-diamine (14 g, 69 mmol) in DMF (702 mL) at room temperature was added CDI (29 g, 180 mmol). The reaction mixture was stirred for 16 h. LCMS analysis of the crude reaction mixture showed that the reaction was not complete, and the resultant residue was re-dissolved in THF and CDI (11.2, 69 mmol) was added. The reaction mixture was stirred at 60 C for 16 h. The reaction mixture was quenched with water and diluted with Et2O. The suspension was filtered and the resulting solid was washed with Et2O and dried under vacuum to yield the title compound as a black solid (15.8 g, 35.7 mmol), which was used in the next step without further purification. MS (ESI): mass calcd. for C7H6BrN3O, 226.97; m/z found, 227.0 [M+H]+.

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHROVIAN, Christa C.; LETAVIC, Michael A.; RECH, Jason C.; RUDOLPH, Dale A.; JOHNSON, Akinola Soyode; STENNE, Brice M.; WALL, Jessica L.; (533 pag.)WO2018/67786; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem