Month: April 2022

Related Products of 928653-73-0 ,Some common heterocyclic compound, 928653-73-0, molecular formula is C5H2BrClIN, 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 : Sodium hydride (2.0 equiv.) was added to dioxane (0.3 M). 2- ((tetrahydro-2H-pyran-2-yl)oxy)ethanol (2.0 equiv.) was added and the mixture was stirred for 30 min at rt. 5-bromo-2-chloro-3-iodopyridine (1.0 equiv.) was added to the mixture and the reaction was heated to 105 C for 1 hour. The cooled reaction mixture was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel (heptanes with 10% ethyl acetate) to give 5-bromo-3-iodo-2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy )pyridine as a colorless oil in 78% yield. LCMS (m/z) (M+H) = 427.8/429.8, Rt = 1.12 min.

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. 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; LOU, Yan; NISHIGUCHI, Gisele A; RAMURTHY, Savithri; RICO, Alice C.; RAUNIYAR, Vivek; SENDZIK, Martin; SUBRAMANIAN, Sharadha; SETTI, Lina Quattrocchio; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (307 pag.)WO2016/38582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 619331-71-4 ,Some common heterocyclic compound, 619331-71-4, molecular formula is C7H4Br2N2, 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 mixture of 2u (2.0 g, 7.3 mmol) and CuCN (1.0 g, 11 mmol) was added DMF (20 ml). The reaction mixture was heated at 150 C. for 1 hour. After cooling to room temperature, the reaction mixture was added NaOMe (20 ml, 25 wt. % solution in MeOH), and was heated at 110 C. for 10 minutes. After cooling to room temperature, the reaction mixture was poured into an aqueous solution of ammonium acetate (sat. 500 ml). The resulting mixture was filtered through a short Celite pad. The filtrate was extracted with EtOAc (500 ml×4). The combined extracts were dried over MgSO4 and evaporated in vacuo to give a brownish residue, which was triturated with MeOH (5 ml×3) to provide precursor 2v as a yellow solid (317 mg, 25%). The structure was supported by NOE experiments. 1H NMR: (DMSO-d6) 12.47 (s, 1H), 8.03 (s, 1H), 7.65 (t, J=2.8, 1H), 6.70 (dd, J=2.8, 1.8, 1H), 4.08 (s, 3H); LC/MS: (ES+) m/z (M+H)+=174; HPLC (alternate conditions B, column G) Rt=1.320.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,619331-71-4, its application will become more common.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

A 100-mL round bottom flask equipped with a magnetic stirrer was charged with 2-chloro-5-(trifluoromethyl)pyridine-3-amine (1.0 g, 5.1 mmol), CH2Cl2 (15 mL), TEA (1.42 ml, 10.2 mmol). The reaction mixture was cooled under ice-bath and chloroacetyl chloride (0.81 ml, 10.2 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under vacuum. The residue was purified by column chromatography using 20% EtOAc/hexane to afford the desired product as off-white solid (1.22 g, 88% yield).). 1H NMR (300 MHz, CDCl3) delta: 9.05 (s, 2H), 8.44 (s, 1H), 4.27 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Zhang, Yongzheng; Kaul, Malvika; US2015/133465; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 194673-12-6, 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 194673-12-6 as follows.

A solution of 6-hydroxy-2-trifluoromethyl-4,5-dihydro-pyridine-3-carboxylic acid ethyl ester (Description 16) (4.7 g, 19.8 mmol, 1 eq) and N-bromosuccinimide (3.51 g, 19.8 mmol, 1 eq) in 15 ml of carbon tetrachloride was heated under reflux for 20 h. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a brownish solid that was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9:1 to hexane/ethyl acetate 8:2). The title compound was obtained as a white solid (4.3 g, yield = 92%). LC-MS (ESI+), MH+: 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,194673-12-6, its application will become more common.

Reference:
Patent; Glaxo Group Limited, Glaxo Group Limited; WO2004/29027; (2004); A1;,
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.182275-70-3, name is 2-Iodo-6-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.category: pyridine-derivatives

EXAMPLE 20.1 (+-)-3-[(6R,8aS-6-[(6-methoxypyridin-2-yl)ethynyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]pyrazine-2-carbonitrile A mixture of 3-[(6R,8aS)-6-ethynylhexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]pyrazine-2-carbonitrile (300 mg, 1.18 mmol), 2-iodo-6-methoxypyridine (278 mg, 1.18 mmol), tetrakis(triphenylphosphine)palladium(0) (137 mg, 0.118 mmol), copper iodide (46 mg, 0.24 mmol), diisopropylethylamine (0.45 mL, 2.6 mmol) and DMF (40 mL) was stirred at RT overnight. 5% EDTA.Na2.2H2O(aq) (2 mL) was added and the reaction mixture was stirred at room for additional 30 min and then concentrated. Flash column chromatography gave the title compound (280 mg, 65%). 1H NMR (400 MHz, CDCl3): delta (ppm) 8.26 (d, 1H), 8.02 (d, 1H), 7.50 (t, 1H), 7.08 (d, 1H), 6.70 (d, 1H), 4.60 (t, 2H), 3.96(s, 1H), 3.52 (d, 1H), 3.38-3.26 (m, 2H), 3.02 (t, 1H), 2.38-2.18 (m, 3H), 2.14-2.04 (m, 1H), 2.00-1.90 (m, 1H), 1.72-1.60 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,182275-70-3, 2-Iodo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/37817; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51454-63-8, 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. 51454-63-8, name is 2-(Hydroxymethyl)isonicotinonitrile, molecular formula is C7H6N2O, 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.

The product of the previous step (1.4 g, 10.2 mmol) and N,N’-dicyclohexylcarbodiimide (6.2 g, 30.0 mmol) were added to a mixture of DMSO (22 ml) & anhydrous H3PO4 (0.45 g) and the reaction was left to stir 1.5 hours. The reaction was filtered and washed with diethyl ether (2 x 30 ml) and water (2 x 30 ml). The reaction layers was separated and the organic layer was washed with saturated brine (2 x 30 ml), dried with MgS04, filtered and evaporated in vacuo to yield (iid) as a yellow solid which was taken towards the next step without purification.

According to the analysis of related databases, 51454-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
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.124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.COA of Formula: C8H6F3NO2

IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of methyl 5-trifluoromethyl-pyridine-2-carboxylate (2 g, 9.75 mmol) in MeOH (30 mL) at 0C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93% yield): 1H NMR (400 MHz, CDC13) delta ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124236-37-9, Methyl 5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHRISTENSEN, IV, Siegfried Benjamin; WU, Chengde; ZHANG, Zhiliu; YU, Haiyu; YUAN, Jiangxing; LIN, Xiaojuan; XU, Shanli; LV, Maoyun; YAO, Chen; LI, Lei; HUANG, Xing; GAO, Min; WO2013/166621; (2013); 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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of 5-bromo-3-chloro-2-methylpyridine (1.03 g, 5 mmol) and (i-PrO)3B (2.24 mL, 10 mmol) in THF (10 mL) was added n-BuLi (3.75 mL, 1.6 M in hexane, 6 mmol) drop-wise at – 78 oC. After the mixture was stirred at -78 oC for 1 hr, it was quenched with water. The solvent was removed under reduced pressure and the aqueous layer was washed with Ether (2 x 10 mL). The aqueous layer was then adjusted to pH~8 with 1N aqueous HCl solution and extracted with EA (3 x 50 mL). The combined organic layers were dried over Na2SO4, and concentrated to give 5-chloro-6-methylpyridin-3-ylboronic acid (650 mg, 76% yield) as a white solid. Retention time (LC-MS): Retention 0.458 min. MH+ 172

The synthetic route of 914358-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertand, L.; WU, Xinyuan; (351 pag.)WO2016/44792; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77199-09-8, 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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.

General procedure: Ester (FAE, 4a-m, 2a or 2b) (500 mg scale, 1 equiv.) was dissolvedin 6 ml THF at 0 C in a 25 ml round-bottom flask. ThenNaOH(aq) (5 equiv.) was added dropwise and stirred for 15 h atroom temperature. After starting materials were consumed (byTLC), water (20 ml) was added. The reaction mixture was washedwith ethyl acetate (2 x 20 ml). The aqueous solution was acidified(pH 2-3) with 1 M HCl(aq) causing precipitation of a solid, whichwas filtered and dried under vacuum. Recrystallization in ethanolafford clean compound.

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 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
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. 54-92-2, name is N’-Isopropylisonicotinohydrazide. A new synthetic method of this compound is introduced below., Safety of N’-Isopropylisonicotinohydrazide

To solution containing (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid (200.0 mg, 0.70 mmol), N?-isopropylisonicotino hydrazide (188.2 mg, 1.05 mmol) and HATU (399.2 mg, 1.05 mmol) dissolved in DMF (5.0 ml), N,N-diisopropylethylamine (DIPEA)(0.18 ml, 1.05 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc=3:1) for refinement and dried so that ivory (E)-tert-butyl 3-(3-(2-isonicotinoyl-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (108 mg, 34.4%). [0353] 1H-NMR (MeOD, 500 MHz): delta 8.87 (2H, d, J=4.6 Hz, aromatic), 8.18 (1H, d, J=8.3 Hz, aromatic), 7.95 (3H, m, aromatic), 7.84 (1H, d, J=15.7 Hz, indole-CH?CH-), 7.58 (1H, m, aromatic), 7.34 (1H, t, J=7.6 Hz, aromatic), 7.13 (1H, m, aromatic), 6.96 (1H, d, J=15.2 Hz, indole-CH?CH-), 5.03 (1H, m, -N-CH-(CH3)2), 1.71 (9H, s, Boc), 1.33 (6H, m, -N-CH-(CH3)2)

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, 54-92-2, N’-Isopropylisonicotinohydrazide.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; LEE, Hyun Sun; KIM, Mun-Ock; CHOI, Yongseok; Lee, Kyeong; PARK, Jeong-Jun; SEO, Jee-Hee; JUNG, Hwayoung; CHO, Sungchan; US2014/57909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem