Tag: M.W=300-400

Related Products of 16727-47-2 , The common heterocyclic compound, 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, 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 1-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2- one 44-3 (200mg, 1.30 mmol), 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (481 mg, 1.30 mmol) and K2CO3 (539 mg, 3.90 mmol) in dioxane / H2O (2ml, 4:1, v/v) was thoroughly degassed under argon followed by addition of Pd2(dba)3 (119 mg, 130 mumol) and tri-tertiarybutylphosphine tetrafluoroborate (75.4 mg, 260 mumol) and finally heating at 100 0C overnight. The reaction mixture was filtered over Celite, the filtrate was concentrated and the crude residue was purified by flash column chromatography to afford 2′,6′-bis(benzyloxy)-1-methyl-[3,3′-bipyridin]-2(1H)-one (44-4) (120 mg, 301 mumol, 23.2 %). LC MS: ES+ 399.2

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 79491-46-6 ,Some common heterocyclic compound, 79491-46-6, molecular formula is C6H4Br2N2O3, 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.

E4. 2-Bromo-5,6-dimethoxy-3-nitropyridine 20 g of 2,6-dibromo-3-methoxy-5-nitropyridine (example E3) are dissolved in 550 ml of anhydrous methanol at 30-40 C. 4.6 g sodium methoxide dissolved in 30 ml anhydrous methanol is added to this solution. The reaction mixture is stirred for one hour at room temperature, poured into 700 ml of water and stored in the refrigerator overnight. The precipitate is filtered, washed with ice cold water and dried under vacuum to yield the title compound. 1H NMR (400 MHz, CDCl3): delta = 3.95 (s, 3H), 4.12 (s, 3H), 7.69 (s, 1 H). 13C NMR (100 MHz, CDCl3): delta = 55.68, 56.73, 115.33, 121.89, 143.18, 155.10.

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. 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53710-18-2 , The common heterocyclic compound, 53710-18-2, name is 3,5-Diiodopyridine, molecular formula is C5H3I2N, 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.

GammaAlpha1 6-Chloro-2-(5-iodo-3-pyridyl)-3,4-dihvdroisoquinolin-l-one A mixture of 6-chloro-3,4-dihydro-2H-isoquinolin-l-one (intermediate A-1, 380 mg, 2 mmol), 3,5-diiodopyridine (1.192 g, 3.6 mmol), Cul (152 mg, 0.8 mmol), (IS, 2S)- cyclohexane-l,2-diamine (182.4 mg, 1.6 mmol) and K3PO4 (848 mg, 4 mmol) in dioxane (5 mL) was heated to reflux temperature for 3 hours. After cooling to room temperature, the mixture was poured into satd. aq. NaHC03 solution (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product, which was then purified by silica gel flash chromatography to afford the title compound (350 mg, 46%) as a white solid. MS: 385.1 (M+H+).

The synthetic route of 53710-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000025-07-9, 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 1000025-07-9, name is Vadadustat. This compound has unique chemical properties. The synthetic route is as follows.

Vadadustat (4.0g), L-Proline (2.85g) and acetone (60mL) were charged in a RBF at 25±5C and the contents were heated to 60-65C and stirred for 60 minutes at 60-65C. The reaction mass was slowly cooled to 25±5C and maintained under stirring at 25±5C for 16 hours. The product obtained was filtered, washed with acetone (8 mL) and dried under vacuum for 16 hours at 40C. The solid obtained was identified as 1 :2 co-crystal of Vadadustat L-Proline. Yield: 6.1 g

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 1000025-07-9, Vadadustat.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59020-10-9 ,Some common heterocyclic compound, 59020-10-9, molecular formula is C17H31NSn, 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 alcohol 348 (310 mg, 1.21 mmol), 3- (tributyl) stannylpyridine (446 mg, 1.21 mmol), Pd (DPPF) 2CL2 (59 mg, 0.072 mmol), copper (I) chloride (12 mg), lithium chloride (305 mg, 7.20 mmol) in DMSO (3.0 mL) was degassed by argon and then was stirred at 60C for 16 h. The reaction was quenched by the addition of H20 (50 mL), NH40H (0.2 mL), EtOAc (150 mL) and CH2C12 (20 mL). The mixture was passed through celite. The organic layer was washed with water (50 ML x 3), dried with NA2S04, and the residue was purified by flash- chromatography (eluant: MEOH/CH2CL2, 2/100), to give 488 (265 mg). Data for 488 : 1HNMR (300 MHz, CDC13) : 8 8.88 (s, 1H), 8.63 (d, J= 4 Hz, 1H), 7.92 (d, J= 8 Hz, 1H), 7.89 (d, J= 8 Hz, 2H), 7.64 (d, J= 8 Hz, 1H), 7.41 (dd, J= 8,5 Hz, 1H), 4.92 (dddd, J= 12,8, 3,3 Hz, 1H), 3.92 (dd, J= 12,3 Hz, 1H), 3.72 (dd, J= 12,5 Hz, 1H), 3.44 (dd, J= 17,11 Hz, 1H), 3. 33 (dd, J = 17,8 Hz, 1H).

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. 59020-10-9, 3-(Tributylstannyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RIB-X PHARMACEUTICALS, INC.; WO2004/29066; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8 , The common heterocyclic compound, 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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 1-11 (4.30 g, 12.57 mmol) , bis (pinacolato) diboron (3.82 g 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (50 mL x 3) . The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2SC> and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1- XIII as a mixture of minor boronate ester together with major boronic acid . (4.8 g, crude yield 98%) as a yellow solid; LCMS (for boronate ester) : m/z 390.2 [M+l]; LCMS (for boronic acid) : m/z 308.1 [M+l] .

The synthetic route of 153747-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (284 pag.)WO2015/88045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-96-5, 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 1221171-96-5, name is 2-Chloro-4-iodo-6-(trifluoromethoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-6-trifluoromethoxy isonicotinic acid (43); At 0 0C, butyllithium (1.56 M in hexane, 4.0 mL, 6.2 mmol, 0.67 eq) was added dropwise to a solution of butylmagnesium chloride (2M in THF, 1.5 mL, 3.0 mmol, 0.33 eq) in THF (8 mL), followed after 10 min by a solution of 2-chloro-4-iodo-6- trifluoro?iepsilonthoxypyridinepsilon (42, 3.0 g, 9.3 mmol, 1 eq) in THF (5 mL). After 10 min the reaction mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6 N, 5 mL). After extraction with ethyl acetate (3 x 10 mL), the combined organic layers were dried over sodium sulfate before being evaporated to afford pure 2-chloro-6-trifluoromethoxy isonicotinic acid (43, 1.6 g, 6.6 mmol, 71%) as a white powder; m.p. 65-68 0C.1H NMR (CDCl3, 300 MHz): delta = 10.12 (br s, 1 H), 7.88 (d, J = 0.9 Hz, 1 H), 7.56 (d, J = 0.9 Hz, 1 H). – 19F NMR (CDCl3, 282 MHz): delta = -57.3 – 13C NMR (CDCl3, 75 MHz): delta = 167.6, 156.3, 150.4, 143.0, 122.5, 120.2 (q, J = 260 Hz), 113.5. – C7H3ClF3NO3 (241): calcd. (%) C 34.81, H 1.25, N 5.80; found C 34.64, H 1.55, N 5.76.

According to the analysis of related databases, 1221171-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 173528-92-2, 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. 173528-92-2, name is HMN-154. A new synthetic method of this compound is introduced below.

Example 1 (E)-4-[2-{2-[N-phenoxycarbonyl-N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine 1.00 g of (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine was suspended in 40 ml of chloroform and, after adding 1.82 g of phenyl chlorocarbonate, 1.20 g of triethylamine was slowly added under ice cooling. Then, the mixture was stirred at room temperature for 5 minutes. The solvent was distilled off under reduced pressure and the desired product was purified by silica gel column (carrier:Wako Gel C200, developing solvent chloroform) to obtain the desired compound. The desired compound was treated with ethanol to obtain 0.71 g of a white granular crystal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,173528-92-2, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1382335; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 875781-18-3, 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. 875781-18-3, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine ((II), 10.44 g, 32.2 mmol) was combined with DMF, MeOH and triethylamine (75 mL each). The vessel was evacuated and flushed with argon (4x). XantPhos (1.12 g, 1.93 mmol) and Pd(OAc)2 (217 mg, 0.97 mmol) were added and carbon monoxide (generated from formic acid and sulfuric acid) was bubbled through the solution while heating to 60 C. The mixture was stirred under an atmosphere of carbon monoxide (balloon) for 8 h. Every 1.5 h carbon monoxide was bubbled through the solution for 5 minutes. The mixture was concentrated under reduced pressure and the residue was triturated with 2N HCl. The solids were heated at 95 C in about 100 mL 1N NaOH overnight. After cooling to RT, the mixture was acidified with conc. HCl and the precipitate collected by suction filtration and washed with water. The solids were dried in an oven at 110 C to constant mass. The solids were sonicated in 100 mL of toluene for 5 minutes and stirred for 30 minutes. The product was filtered, washed with an additional 20 mL of toluene and dried at 110 C. Yield: 7.92 g HPLC purity: > 99 %, 1H NMR (200 MHz, DMSO) delta 8.64 (d, J = 7.9 Hz, 2H), 5.69 (bs, 1H); 13C NMR (50 MHz, DMSO) delta 163.27, 150.97, 149.67, 136.69, 132.65, 115.73, 113.6; [M-H]- = 239.9 / 241.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,875781-18-3, 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138647-49-1, tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate, 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, Recommanded Product: 138647-49-1, blongs to pyridine-derivatives compound. Recommanded Product: 138647-49-1

B. Methyl 1-boc-1,2,3,6-Tetrahydro-4-pyridinecarboxylate To a stirred solution of 1-Boc-1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine (74.84 g, 226 mmol) in N,N-dimethylformamide (60 mL) was added triethylamine (4.2 mL, 30.2 mmol), palladium acetate (0.100 g, 0.45 mmol), triphenylphosphine (0. 235 g, 0.9 mmol), and methanol (24.5 mL) and the solution was placed under an atmosphere of carbon monoxide. After stirring for 48 h, the solvent was removed in vacuo. The residue was chromatographed over silica gel, eluding with 5-10% ethyl acetate in hexane. The product containing fractions were combined and concentrated in vacuo to give 2.35 g (65%) of the title compound as a clear oil. 1H-NMR; FD-MS, m/e 240.2 (m); Analysis for C12H19NO4: Calcd: C, 59.74; H, 7.94; N, 5.81; Found: C, 59.60; H, 8.07; N, 5.85.

The synthetic route of 138647-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6635657; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem