Month: April 2022

Electric Literature of 128071-79-4 ,Some common heterocyclic compound, 128071-79-4, molecular formula is C6H5BrFN, 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 sealable reaction flask containing a solution of Intermediate 15E (9.90 g,33.7 mmol) in Dioxane (195 mL) was added 4-bromo-2-fiuoro-3-methvlpyridine (6.21 g, 32.7 mmoi), Water (65.0 mL) and Na2CO3 (13.86 g, 131 inmol). After the mixture was degassed with Argon for 10-15mm, Pd(Ph3P)4 (1.888 g, 1634 mmoi) was added, the flask was sealed and the mixture was heated to 100 C for 24 hours, then allowed to slowly cool to rt. Reaction was diluted with EtOAc and water, plus sonication to break up solids, then transferred to a sep funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2SO4, filtered and concentrated in vacuo to afford a dark brown residue. Purified on silica gel colunm chromatography to give Intermediate 23A (7.23 g, 26.1 minol, 80% yield). LC-MS Anal. Calc?d for CI6H20FNO2 277.15, found [M+Hj 278.2, Tr = 104 mm (Method A).

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. 128071-79-4, 4-Bromo-2-fluoro-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Emily Charlotte; SHAN, Weifang; ZHANG, Liping; NARA, Susheel Jethanand; HUANG, Audris; BALOG, James Aaron; (129 pag.)WO2018/39512; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166266-19-9, Adding some certain compound to certain chemical reactions, such as: 166266-19-9, name is 5-Iodo-3-methylpyridin-2-amine,molecular formula is C6H7IN2, 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 166266-19-9.

Production Example 4: Production of 2-amino-3-methyl-6-pentafluoroethylpyridine (Compound No. IV-1) To 20 ml of dimethyl sulfoxide were added 2.34 g (0.01 mol) of 2-amino-5-iodo-3-methylpyridine, 2.5 g of powdered metallic copper and 3.7 g (0.015 mol) of iodopentafluorethane. The mixture was kept at 110C and vigorously stirred for 6 hours. After cooling the reaction mixture to room temperature, the mixture was poured into 500 ml of ice water and thoroughly stirred. The insoluble matter was filtered off, and the objective product was extracted from the filtrate with 300 ml of ethyl acetate. The extract solution was washedwith water, dried on anhydrous sodium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography using 3/7 mixture of ethyl acetate and hexane as an eluent gave 1.1 g of the objective product (yield 20%). 1H-NMR [delta (CDCl3)]: 2.17 (s,3H), 4.82 (br,2H), 7.42 (d,1H), 8.16 (s,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. 166266-19-9, 5-Iodo-3-methylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; EP1193254; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1226878-98-3 , The common heterocyclic compound, 1226878-98-3, name is 2-Chloro-5-iodo-4-methoxypyridine, molecular formula is C6H5ClINO, 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.

j00505j To a solution of compound B-116 (4.0 g, 7.4 mmol) in acetic acid (30 mL) was added hydrogen bromide (40% in water, 23 g, 11 immol). The vessel was sealed and heated to 110 C for 4 hours. On completion, the mixture was concentrated in vacuo. The residue was dissolved in methanol (20 mL) and triethylamine (20 mL), concentrated again in vacuo and purified by silica gel chromatography [dichloromethane: methanol = 30:11 to give compound B-117 (3.0 g, 75% yield) as a white solid. ?H-NMR (CD3OD, 400 MHz): 8.33 (s, 1H), 6.73 (s, 1H).

The synthetic route of 1226878-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17282-01-8, 3-Bromo-2-fluoro-5-picoline, 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, 17282-01-8, blongs to pyridine-derivatives compound. Recommanded Product: 3-Bromo-2-fluoro-5-picoline

Preparation 98: 5-(2-Fluoro-5-methylpyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep98); 2,4-Dimethoxy-pyrimidine-5-boronic acid (842 mg, 4.60 mmol) was dissolved in degassed n-PrOH (55 ml) and then 2-fluoro-3-bromo-5-methylpyridine (800 mg, 4.21 mmol), Na2CO3 (1.46 g, 13.77 mmol), PPh3 (348 mg, 1.33 mmol) and Pd(OAc)2 (101 mg, 0.45 mmol) were added. The suspension was stirred at reflux for 2 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The residue was triturated with Et2O to give 350 mg of the title compound as a gray powder (31 % yield). MS (ES) (mlz): 250.2 [IvRH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-01-8, its application will become more common.

Reference:
Patent; Glaxo Group Limited; WO2007/113232; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 117846-58-9 , The common heterocyclic compound, 117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, 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 1: 2-(4-(6-Bromo-3,5-dimethylpyridin-2-ylamino)piperidin-1-yl)benzonitrile A mixture of 2-(4-amino-1-piperidyl)benzonitrile (3.00 g, 14.91 mmol), 2,6-dibromo-3,5-dimethyl-pyridine (4.74 g, 17.89 mmol), tBuONa (2.15 g, 22.36 mmol), Pd2 (dba)3 (136.53 mg, 149.05 umol) and BINAP (278.43 mg, 447.16 umol) in toluene (50.00 mL) was stirred at 80 C. for 17 h. The mixture was filtered and purified by silica gel chromatography to afford 2-(4-(6-bromo-3,5-dimethylpyridin-2-ylamino)piperidin-1-yl)benzonitrile (2.10 g, 5.45 mmol, 36.55% yield) as product. ESI-MS (EI+, m/z): 385.1 [M+H]+.

The synthetic route of 117846-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 52605-96-6, name is 2-Chloro-3-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. category: pyridine-derivatives

(b). 2,3-dimethoxypyridine To a solution of 2-chloro-3-methoxy-pyridine (1 10 g) in DMSO (1 L) was added sodium methoxide (124 g). The reaction mixture was heated to 80C overnight. The reaction mixture was poured into 3 L water and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product. Yield: 105 g ? NMR delta (ppm)(CH3OH-d): 7.70 (t, 1 H, J=1.2 and 5.2 Hz), 7.01 (t, 1 H, J=1.2 and 8.0 Hz), 6.81 (q, 1 H, J=5.2 and 7.8 Hz), 4.00 (s, 3H), 3.85 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 52605-96-6.

Reference:
Patent; MSD OSS B.V.; BLACKABY, Wesley, Peter; DE KORT, Martin; ENTHOVEN, Mark; HINCHLIFFE, Paul, Stuart; PAULIE, Chris; TIMMERS, Cornelis, Marius; VERKAIK, Saskia; WO2013/41458; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5, 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. 1227573-02-5, name is 3-Bromo-5-fluoroisonicotinaldehyde, molecular formula is C6H3BrFNO, 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 3-bromo-5-fluoroisonicotinaldehyde (0.656 g, 3.22 mmol) in THF (5 mL) was added prop-1-yn-1-ylmagnesium bromide (0.5 M in THF, 8.36 mL, 4.18 mmol) solution at 0 C. After stirring at 0 C. for 2 h, excess sat. aq. NaHCO3 solution was added to quench the reaction mixture followed by extracting with EtOAc twice and DCM twice. All organic layers were combined and dried over anhydrous Na2SO4. The solid was filtered out. Volatiles were removed under reduced pressure to afford the title compound (0.78 g, 99%). It was used directly in the next step without further purification. ESI-MS m/z: 245.9 [M+H]+ (Rt=0.92 min., LC-method 3)

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 1227573-02-5, 3-Bromo-5-fluoroisonicotinaldehyde.

Reference:
Patent; NOVARTIS AG; BARBE, Guillaume; BEBERNITZ, Gregory Raymond; GENG, Sicong; GULGEZE EFTHYMIOU, Hatice Belgin; LIAO, Lv; MA, Fupeng; MO, Ruowei; PARKER, David Thomas; PENG, Yunshan; PEUKERT, Stefan; YAMADA, Ken; YASOSHIMA, Kayo; (78 pag.)US2018/111932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5453-67-8, 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 5453-67-8 as follows.

Step 1: Preparation of methyl 6-formylpyridine-2-carboxylate (I-33a) A suspension of dimethylpyridine-2,6-dicarboxylate (1.0 g, 5.12 mmol) in methanol (8 mL) and THF (3 mL) was heated at 75 C. until the solid was dissolved. NaBH4 (184 mg, 4.87 mmol) was then added portion-wise. The mixture was stirred at 70 C. for 1 h. The mixture was cooled to room temperature and 10% citric acid (1.6 mL) was added. The solution was filtered and the filtrate was evaporated to dryness, taken up in dichloromethane, dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-100% EtOAc in isohexane, to provide a colourless oil which was then dissolved in toluene (20 mL) and chloroform (20 mL). MnO2 (194 mg, 22.2 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered through a pad of fluorosil, eluting with chloroform (30 mL) and the solvent was removed in vacuo to provide the title compound (249 mg, 29%) as white solid. 1H NMR (400 MHz, CDCl3): delta 10.20 (s, 1H), 8.37 (dd, J=1.2, 7.6 Hz, 1H), 8.17 (dd, J=1.2, 7.6 Hz, 1H), 8.08-8.04 (m, 1H), 4.07 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5453-67-8, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]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, 92276-38-5, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3BrN4

To a suspension of NaH (60% in mineral oil, 120 mg, 3.0 mmol) in THF (3 mL) at 0C was added 6-bromo-1 H-[1 ,2,3]triazolo[4,5-£>]pyridine (400 mg, 2.0 mmol) in THF (8 mL). The mixture was stirred at 0C for 30 min, then SEM-CI (500 mg, 3.0 mmol) was added at 0C dropwise and stirring was continued for 1 h. The reaction was quenched with NH4CI (sat.) and extracted with EtOAc (3 x 20 mL). The organic layers were combined and washed with brine (2 x 20 mL), dried over Na2S04, concentrated and purified by chromatography to give lnt-6-11 as a mixture of 6- bromo-1 -((2-(trimethylsilyl)ethoxy)methyl)-1 H-[ ,2,3]triazolo[4,5-i>]pyridine and 6-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-[1 ,2,3]triazolo[4,5- ?]pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92276-38-5, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1111637-94-5 , The common heterocyclic compound, 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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 solution of 19 (100 mg, 0.434 mmol) and 52 (118.2 mg, 0.434 mmol) in toluene/ ethanol (4:1) was added sodium carbonate (95.04 mg, 0.868 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (17.72 mg, 0.0217 mmol) was added to the reaction. The reaction mass was degassed and purged with nitrogen for another 10 min. The reaction was heated to 80 C. under sealed condition overnight. The reaction was allowed to cool to rt and diluted with chloroform. The organic layer was filtered through Celite bed and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 2% methanol in chloroform as off-white colour solid compound 53. MS-ES+ 277.9; 1H NMR (400 MHz, DMSO-D6) 53: 11.31 (s, 1H), 9.46 (s, 1H), 8.12 (d, 1H), 7.83 (d, 1H), 7.56 (d, 1H), 7.33 (m, 4H), 7.24 (bs, 1H), 6.30 (m, 1H), 6.11 (m, 1H), 5.62 (m, 1H), 2.22 (s, 3H).

The synthetic route of 1111637-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem