Day: September 16, 2021

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. 891785-18-5, name is 3-(Benzyloxy)-5-bromo-2-chloropyridine, molecular formula is C12H9BrClNO, 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. Computed Properties of C12H9BrClNO

To a suspension of 68 3-(benzyloxy)-5-bromo-2-chloropyridine (25.7 mg, 86.0 mmol) and 41 potassium phosphate (54.9 g, 259 mmol) in 9 tetrahydrofuran (180 mL) were added successively 14 water (130 mL), 17 (E)-2-(3-methoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.1 mL, 95.0 mmol) and [1,1?-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (3.54 g, 4.33 mmol), and the mixture was stirred at room temperature for 2 hr. [1,1?-Bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (1.70 g, 2.04 mmol) was added again thereto, and the mixture was stirred at room temperature for 3 hr, warmed to 33 C., and stirred for 1 hr. The reaction solution was diluted with ethyl acetate (180 mL), and the insoluble substance was removed by filtration. The organic layer of the filtrate was washed with water and saturated brine, silica gel (50 g) was added thereto, and the mixture was stirred at room temperature for 1 hr. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=15:1 to 4:3) to give 70 (E)-3-(benzyloxy)-2-chloro-5-(3-methoxyprop-1-en-1-yl)pyridine (20.9 g, yield 83%). 1H-NMR (DMSO-D6) delta: 3.29 (3H, s), 4.06-4.07 (2H, m), 5.29 (2H, s), 6.59-6.60 (2H, m), 7.32-7.49 (5H, m), 7.81 (1H, d, J=1.8 Hz), 8.02 (1H, d, J=2.1 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 891785-18-5.

Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 19798-80-2, name is 4-Chloropyridin-2-amine. A new synthetic method of this compound is introduced below., Formula: C5H5ClN2

Step 1 : To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 C for 3 hours then poured into ice- water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2S04) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2 -amine (460 mg, 16%) as a yellow solid MS ESI calcd for C6H8N20 [M + H]+ 125, found 125.

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, 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ROMEO, Eric Thomas; MACHACEK, Michelle, R.; TROTTER, Benjamin Wesley; MILLER, Thomas Allen; ANDRESEN, Brian Michael; ANTHONY, Neville John; TAOKA, Brandon, M.; LIU, Yuan; WO2012/151137; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15855-06-8, 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. 15855-06-8, name is 2-Chloro-6-methoxypyridine-4-carboxylic Acid. A new synthetic method of this compound is introduced below.

BH3. DMS (1.0 mL, 10.66 mmol) was refluxed in THF (20 mL) for 30 min (formation of BH3. THF). At RT, Example 17 (2.0 g, 10.66 mmol in 10 mL THF) was added dropwise, and then the reaction mixture was heated to reflux for 3 h. The solution was allowed to cool to ambient temperature, solid sodium carbonate (0.5 g) and water (5 mL). The resulting mixture was heated for a short while and poored in water (50 mL). Extraction with ethyl acetate (3 x 50 mL), drying of the combined organic layers (Na2SO4) and evaporation in vacuo gave a 1: 1 mixture of starting material and product. Purification by flash column chromatography over silica gel eluting with ethyl acetate gave 780 mg (42 %) of an off-white solid. IH NMR (400 MHz, CDC13) 8 3.92 (s, 3H) 4.66 (s, 2H) 6.64 (s, 1H) 6.89 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15855-06-8, 2-Chloro-6-methoxypyridine-4-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; BIOVITRUM AB; WO2004/63156; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75711-00-1 , The common heterocyclic compound, 75711-00-1, name is 2-Chloro-3-methoxy-5-nitropyridine, molecular formula is C6H5ClN2O3, 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.

Synthesis of 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine [0328] To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (40 mL) under argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-lH-imidazole (1 g, 12.72 mmol) at RT. The reaction mixture was stirred at 45 C for 16 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with hot water (40 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-<, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+l); (column; X-Bridge C- 18 (50 3.0 mm, 3.5 mu); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH:CH2Cl2 (R 0.4). The synthetic route of 75711-00-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 872365-91-8, name is 2-Bromo-6-(difluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H4BrF2N

To a stirred solution of 2-bromo-4-fluoropyridine (0.3 g, 1.71 mmol) in 1,4-dioxane (5 mL) was added hexamethylditin (0.43 mL, 2. immol). The reaction mixture was purged with N2 for 10 mm. and to it was added Pd(Ph3P)4 (0.20 g, 0.17 mmol). The reaction mixture was purged once again with N2 for another 10 mm and heated at 110 C for 2 h. Then, after cooling to room temperature, compound 1A (0.43 g, 1.7lmmol) was added and the mixture was purged with N2 for 5 mm., followed by the addition of Pd(Ph3P)4 (0.2 g, 0.17 mmol). The reaction was again heated at 110 C for 18 h. The reaction mixture was concentrated under vacuum to give a crude residue, which was purified by preparative HPLC (Condition N) to provide 6-(4?-fluoro- [2,2?-bipyridinj -3-yl)imidazo [1,2-al pyridine-3 -carbonitrile 16 (0.38 mg, 0.89 mmol, 52.3 % yield). LC-MS: m/z = 317.1 [M+Hf?; ret.time 1.41 mm; condition C. ?H NMR (400 MHz, DMSO-d6) 3 ppm 8.93 – 8.89 (m, 1H), 8.60 – 8.57 (m, 1H), 8.27 – 8.19 (m, 3H), 8.03 – 7.97 (m, 1H), 7.77 – 7.72 (m, 1H), 7.42 – 7.37 (m, 1H), 7.34 – 7.27 (m, 1H). Compound 49 was synthesized by reacting 4 (reference: WO 2015157093 Al and WO 2014055955 Al) and 2-bromo-6-(difluoromethyl)pyridine employing the experimental procedure described in Scheme 4 (Method-D). The crude residue was purified by preparative HPLC (condition-H) to yield 6-(6?-(difluoromethyl)- [2,2?-bipyridinj -3 -yl)imidazo[ 1,2- bjpyridazine-3-carbonitrile 49 (242 mg, 0.0604 mmol, 62.9 % yield). LCMS: m/z = 349.1 [M+Hf?; ret. time 1.53 mm. condition C. ?H NMR (400 MHz, DMSO-d6) oe ppm ppm 8.92 (dd, J4.6, 1.7 Hz, 1H), 8.36 (dd, J8.l, 1.0 Hz, 1H), 8.25 (d, J=9.3 Hz, 1H), 8.21 – 8.18 (m, 2H), 8.16 (t, J=7.8 Hz, 1H), 7.74 (dd, J=7.7, 4.8 Hz, 1H), 7.61 (d, J7.8 Hz, 1H), 7.43 (d, J9.5 Hz, 1H), 6.26 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 872365-91-8.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; BRISTOL-MYERS SQUIBB COMPANY; DING, Pingyu; GELMAN, Marina; KINSELLA, Todd; SINGH, Rajinder; BHAMIDIPATI, Somasekhar; VELAPARTHI, Upender; BORZILLERI, Robert, M.; RAHAMAN, Hasibur; WARRIER, Jayakumar, Sankara; (232 pag.)WO2016/133838; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 108-99-6 ,Some common heterocyclic compound, 108-99-6, molecular formula is C6H7N, 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 2; The pelletized catalyst, TOSOH HSZ-690 HOD (SAR 203) with a silica binder, was ground to a coarse powder and screened to obtain a uniform size of 1-2 mm in diameter. A weight of 0.26 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. Operating at a chlorine feed of 5 cc/min, a beta-picoline feed rate of 0.13 mg/min (10 cc/min N2 with a chiller temperature of 10 C.), the reagents were fed to the reactor at an initial temperature of 250 C. The system was initially ramped up to 325 C. and allowed to stablize. Under these conditions the product gases were 18.5% 3-trichloromethylpyridine (beta-tri ) and 65.4% beta-2-tet. When the system was allowed to stabilized at 350 C. the amount of beta-tri in the product gases was reduced to 2.6% and the conversion to beta-2-tet increased to 68.6% (see Table 2).; Example 3; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm in diameter. A weight of 0.26 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.13 mg/min (N2 flow 10 cc/min, chiller at 10 C.), while the reactor oven was ramped up to 350 C. over a one hour time period. At 350 C. the amount of beta-2-tet observed in the product gases was 65.6% (see Table 2).; Example 4; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm in diameter. A weight of 0.51 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.13 mg/min (chiller at 10 C.), with a nitrogen flow of 10 cc/min, while the reactor oven was ramped up to 350 C. over 2 hours. When the system had stabilized at 350 C. the amount of beta-2-tet observed in the product gases was 71.7% (see Table 2).; Example 5; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm. A weight of 0.51 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.25 mg/min (N2 at 10 cc/min, chiller at 20 C.), while the reactor oven was slowly ramped up to 350 C. over 2 hours. When the system had stabilized at 350 C. the amount of beta-2-tet observed in the product gases was 66.9% (see Table 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108-99-6, its application will become more common.

Reference:
Patent; Campbell, Kent Douglas; Livingston, Dana Alan; Wan, Hawk Suewah; Larson, Kenneth Michael; Schoeman, Brian John; Lakso, Steven Roy; US2005/240024; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82205-58-1, 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. 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine. A new synthetic method of this compound is introduced below.

Step 3: 4-(5-Nitropyridin-2-yl)-N-(2-fluorophenyl)piperazine-l-carboxamide (B-4)To compound B-3 (6.6 g, 32 mmol) dissolved in dry THF (200 mL) was added triethylamine (8.8 mL, 63 mmol) and 2-fluorophenyl isocyanate (4.3 mL, 38 mmol). The resulting reaction mixture was heated at 80 C for 16 h then cooled to RT and concentrated. Water (150 mL) was added, and the aqueous solution was extracted with CH2CI2. The combined organic extract was dried (MgS04), filtered, and concentrated to give a yellow solid. The solid was triturated with water, filtered, and dried to give the product 4-(5-nitropyridin-2-yl)-N-(2- fluorophenyl)piperazine-l-carboxamide (B-4) as a yellow solid (11.4 g, 100% yield). MS (M+1): 346.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82205-58-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Dimethyl pyridine-2,5-dicarboxylate

To a mixture of dimethyl pyridine-2,5-dicarboxylate (3.08 g, 15.78 mmol) and calcium chloride (7.01 g, 63.1 mmol) in tetrahydrofuran (33 mL) and EtOH (67 mL) was added sodium borohydride (1 .493 g, 39.5 mmol) in portions at 0 C. The reaction mixture was stirred at 0 C for 12 hrs. The mixture was poured into ice/water, was diluted with dichloromethane (400 ml.) and stirred vigorously for 15 minutes. The separated organic layer was dried over magnesium sulfate, filtered off and concentrated under reduced pressure providing methyl 6-(hydroxymethyl)nicotinate (1 .2 g) as an off white solid, which was directly used in the next step without further purification. LCMS (m/z): 168.0 [M+H]+; Rt = 0.26 min

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, 881-86-7, Dimethyl pyridine-2,5-dicarboxylate.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 82671-06-5 , The common heterocyclic compound, 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, molecular formula is C6H2Cl2FNO2, 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.

Intermediate[00144] The overall synthetic scheme for the synthesis of5-fluoro-lH-pyrazolo [3, 4-b] pyridin-3-amine 5 is depicted below.1 6 3Reagents and conditions: i. Pd (OAc) 2, PPh3, Et3N, H2CO2; ii. 1) (COCl)2, CH2Cl2, cat. DMF; 2) NH3 (g) , dioxane, iii. TFAA, Et3N, CH2Cl2, 0C; iv. H2NNH2. H2O, n-butanol, reflux2-Chloro-5-fluoronicotinic acid (6)[00145] To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 ?iL) , Pd(OAc)2 (0.05 eq, 2.7 g, 11.9 mmol) , PPh3 (0.1 eq, 6.2 g, 23.8 mmol) , and degassed Et3N (6 eq, 200 mL, 1428.6 mmol) . The mixture was stirred for 20 minutes, HCOOH (3 eq, 28 mL, 714.3 mmol) was then added. 5 minutes later, 2, 6-dichloro-5-fluoronicotinic acid (50 g, 238.1 mmol) was added. The mixture was stirred at 500C. The reaction was followed by analysis (IH NMR) of a worked- up aliquot. When all starting material was consumed (24 h) , the mixture was cooled to 00C and water (500 mL) was added. After 20 minutes, The mixture was filtered through a pad of Celite that was rinsed with water. The mixture was basified to pH 9 with 30% aq. NaOH and washed with EtOAc (2x) . HCl(12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3x) . The combined organic extracts were washed with brine, dried (Na2SO4) , and concentrated under reduced pressure to give 37 g (88%) of a beige solid used in the next step without further purification. 1H NMR (DMSO-de, 300 MHz): delta 8.16 (dd, IH); 8.58 (d, IH).

The synthetic route of 82671-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/112646; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H3BrFNO

[00434] 1A. (R,E)-N-((5-Bromo-2-fluoropyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide: To the solution of 5-bromo-2-fluoronicotinaldehyde (5 g, 24.51 mmol), titanium (IV) ethoxide (15.42 ml, 73.5 mmol) in DCM (49.0 ml) was added (R)-2- methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and the reaction mixture was stirred at rt. After 48 h, the reaction mixture was poured into brine while rapidly stirring to form a suspension. The resulting suspension was filtered through a plug of CELITE, and the filter cake was washed several times with DCM. The filtrate phases were separated, and the organic phase was washed with brine and dried over MgS04. The organic layers were then concentrated to give 7.6 g crude product which was further purified using silica gel chromatography to yield the desired product (6.97 g, 93%) as an off white solid. MS(ESI) m/z: 330.8 (M+Na)+.

With the rapid development of chemical substances, we look forward to future research findings about 875781-15-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem