Month: April 2022

Application of 1403899-44-4 ,Some common heterocyclic compound, 1403899-44-4, molecular formula is C9H11ClN2, 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.

Alternative procedure: Potassium teit-butoxide (600 mg, 5.36 mmol) was added to a stirred solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (800 mg, 4.38 mmol) in anhydrous THF (15 mL) and the mixture was stirred at room temperature for 10 minutes. Asolution of di-teit-butyl dicarbonate (1.07 g, 4.89 mmol) in anhydrous THF (15 mL) was added and the mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo, the aqueous residues were diluted with water (100 mL) and extracted with EtOAc (2 x 200 mL). The organic layers were combined and the solvent was removed in vacuo to afford the title compound (1.19g, 96%), NMR data consistent with those previouslyobtained.

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. 1403899-44-4, 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; MILLEMAGGI, Alessia; HOWARD, Steven; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; WO2014/60768; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189230-41-9, 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 189230-41-9 as follows.

b) Preparation of intermediate 34A mixture of intermediate 33 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated for 1 h at 180 0C. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2Ctheta3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 34, which was used as such in the next reaction step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; BISCHOFF, Francois Paul; ZHUANG, Wei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; MACDONALD, Gregor, James; OEHLRICH, Daniel; WO2010/94647; (2010); 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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-6-methoxypicolinaldehyde

(1) (5R) -5 – [(1,3- benzothiazol-2-ylsulfonyl) methyl] pyrrolidin-2-one (2.80 g), in tetrahydrofuran (170 mL) solution of lithium chloride (824 mg), argon gas atmosphere, at -78 , toluene solution (0.5M, 39mL) of potassium hexamethyldisilazide, and the mixture was stirred at the same temperature for 1 hour. Tetrahydrofuran (10 mL) solution was added to thereto 5-bromo-6-methoxy-pyridine-2-carbaldehyde (1.75g), and stirred at the same temperature for 30 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after filtration, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 50: 50) to give, (5R) -5 – [(Z) -2- (5- bromo-6-methoxy-pyridin-2-yl) ethenyl] pyrrolidin-2-one (900 mg) as a pale yellow oily substance.

The synthetic route of 1206775-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic acid, 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 5,6-Dichloropicolinic acid, blongs to pyridine-derivatives compound. Safety of 5,6-Dichloropicolinic acid

A four-neck 500 milliliter (mL) round bottomed flask was fitted with a thermocouple/J-KEM controller, mechanical stirrer, condenser that vented to a knock-out pot then to a 12% sodium hydroxide (NaOH) scrubber and a stopper. To the vessel was added concentrated sulfuric acid (H2SO4; 27.0 grams (g), 0.28 moles (mol)) and sulfolane (28.9 g). This mixture was warmed to 130 C. and then the solid trichloromethyl-pyridine (70.2 g, 0.26 mol) was added in portions over ca. 1 hour (h). Vigorous degassing to the caustic trap was observed. After the addition was complete, the mixture was stirred at 130 C. for 2 h and then allowed to cool to room temperature with stirring overnight resulting in a thick taffy. The mixture was warmed to 70 C., and a sample was taken for high performance liquid chromatography (HPLC) analysis which indicated a very clean conversion to the corresponding carboxylic acid. To the pot at 70 C. was carefully added isopropyl alcohol (IPA; 83.2 g, 1.39 mol) in portions over about 45 minutes (min) Initially there was vigorous degassing to the NaOH/caustic trap. After the addition was complete, the clear brown solution was stirred at 70 C. for 1 h. The 70 C. solution was added to crushed ice (361 g) with swirling of the flask. At the end of the addition, there was very little ice in the slurry. The slurry was cooled in the refrigerator for 1 h, and the solid was collected via filtration. The cake was washed with IPA/water (31 g/31 g) and then water (65 g). The material was allowed to air dry in a hood to a constant weight providing the product as a light beige solid (55 g, ca. 89%): HPLC purity was 98.5%; EIMS (70 eV) m/z 235, 233 (M+, 1%, 2%), 220, 218, 194, 192, 176, 174, 149, 147 (100%); 1H NMR (400 MHz, CDCl3) 7.98, 7.91 (ABq, J=8.0 Hz, 2H), 5.30 (m, 1H), 1.41 (d, J=4.0 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-24-7, 5,6-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Allen, Laura; Sanford, Melanie; Lee, Shin Hee; Bland, Douglas; Cheng, Yang; Roth, Gary; Muhuhi, Joseck M.; US2015/141654; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53636-70-7, 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 53636-70-7 as follows.

In a 100 ml round-bottomed flask 6-methyl-2,3-pyridinedicarboxylic acid (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D60 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53636-70-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 685115-77-9, 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 685115-77-9 as follows.

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (0.10 g, 0.36 mmol) in polyphosphoric acid (5 ml.) at 80 0C was added vinylene carbonate (35 mg,0.40 mmol). The mixture was heated at 170 0C for 4 hours, cooled to r.t. and poured into water (200 ml_). The mixture was extracted with ethyl acetate (3 x 50 ml.) and the combined organic extracts were washed with water (100 ml_), a saturated solution of sodium hydrogen carbonate (50 ml_), water (50 ml_), brine (50 ml_), dried (MgSO4) and concentrated under reduced pressure to furnish a colourless oil (12 mg). The crude product was purified by preparative tic on silica gel (CH2CI2, MeOH, 10:1 then hexane,EtOAc, 1 :1 ) to furnish the title compound as a white solid (13 mg, 12%), LC-MS (ESI) Rt 2.66 min, m/z 298 (100%, M+); m/z (ESI) Ci3H14CI2N3O requires 298.0508 found [M+H]+ 298.0507.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,685115-77-9, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); 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. 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Chloro-5-iodopyridin-2-amine

A mixture of 4-chloro-5-iodopyridin-2-amine (2.8 g, 1 1 mmol), Pd(PPh3)4 (1.9 g, 1.65 mmol), and Zn(CN)2 (0.7 g, 6.05 mmol) in NMP (30 mL) was heated at 130C for 5 hours. The reaction mixture was cooled to 23C, diluted by H20 (200 mL) and filtered. The solid was purified by silica gel chromatography using Petroleum Ether:EtOAc (3: 1 ) as eluting solvents to afford 2-(3H- imidazo[4,5-b]pyridin-3-yl)acetimidamide as a yellow solid (1.18 g, 70%). MS (ESI) m/z: 154 [M+H]+.

The synthetic route of 670253-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEAUFOUR IPSEN TIANJIN PHARMACEUTICAL CO., LTD; AUVIN, Serge; LAVERGNE, Olivier; CHAO, Qi; CHEN, Yufeng; WO2015/100609; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 91678-23-8, Adding some certain compound to certain chemical reactions, such as: 91678-23-8, name is 2-Bromo-6-chloro-3-nitropyridine,molecular formula is C5H2BrClN2O2, 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 91678-23-8.

Under nitrogen a solution of 2-bromo-6-chloro-3-nitropyridine (2.5 g, 10.53 mmol, 1.00 equiv) in THF (60 mL) was cooled to -78 C. and bromo(ethenyl)magnesium (1M in THF, 63 mL, 6 equiv) was added dropwise. The reaction was stirred for 1 h at -50 C., quenched with aqueous ammonium chloride, extracted with ethyl acetate, dried over sodium sulfate, and concentrated in vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (1.3 g, 53%) as a yellow solid. LC-MS (ES, m/z): 231 [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. 91678-23-8, 2-Bromo-6-chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 274-76-0 ,Some common heterocyclic compound, 274-76-0, molecular formula is C7H6N2, 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 DMF (120 mL, 1.55 mol) at 2 C, freshly distilled phosphorus oxychloride (61 mL, 0.65 mol) was slowly added. The temperature was allowed to rise gradually to room temperature. The solution was cooled again to 2 C and a solution of imidazo[1,2-a]-pyridine 1 (10 g, 0.085 mol) in DMF (60 mL) was added dropwise. The mixture was warmed to 105 C, whereupon the temperature rose to 140 C. The oil bath was removed until the temperature stabilized at 120 C. The reaction mixture was heated for 45 min at 120 C and 2.5 h at 85 C, then cooled and poured into 5% HCl (600 mL) ice-cooled and brought to pH 9 using 20% NaOH. The resulting solution was extracted with CH2Cl2 (1200 mL) overnight. Then the organic layer was separated and dried over MgSO4, the solvent removed under reduced pressure, the crude product washed with water (5 × 15 mL) and again dried, providing the pure product 3.49 g (31%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,274-76-0, its application will become more common.

Reference:
Article; B?aewska, Katarzyna M.; Ni, Feng; Haiges, Ralf; Kashemirov, Boris A.; Coxon, Fraser P.; Stewart, Charlotte A.; Baron, Rudi; Rogers, Michael J.; Seabra, Miguel C.; Ebetino, Frank H.; McKenna, Charles E.; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4820 – 4826;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1235036-15-3, 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 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl 3-bromo-6-chloropicolinate (5.92 g) in tetrahydrofuran (60 mL) and water (30 mL) was added the crude Example 1.20.1 (4.44 g), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (1.5 g), tris(dibenzylideneacetone)dipalladium(0) (927 mg) and K3PO4(22 g). the mixture was stirred at reflux overnight, cooled, diluted with ethyl acetate (800 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. residue was purified by flash chromatography, eluting with 20% ethyl acetate in heptane followed by 5% methanol in dichloromethane, to give the title compound. MS (ESI) m/e 531.1 (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 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate.

Reference:
Patent; AbbVie Inc.; Benatuil, Lorenzo; Bruncko, Milan; Chao, Debra; Izeradjene, Kamel; Judd, Andrew S.; Phillips, Andrew C.; Souers, Andrew J.; Thakur, Archana; (556 pag.)US2017/355769; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem