Tag: M.W:200-300

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

Reference of 1256561-65-5 ,Some common heterocyclic compound, 1256561-65-5, molecular formula is C6H6Br2FN, 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.

Potassium carbonate (193 mg, 1.396 mmol) and 3-(bromomethyl)-5-fluoropyridine hydrobromide (151 mg, 0.558 mmol; Sunshine Chemlab) were added to a solution of 2.2.7-trifluoro-8-(1-hydroxyethyl)-2H-1 ,4-benzoxazin-3(4H)-one (138 mg; may be prepared as described in intermediate 1 1 ) in dry DMF (5 ml_). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was dissolved in DCM (3 ml.) and 10% w/v aqueous citric acid (2 ml_). The layers were separated and the aqueous was extracted with DCM (2 x 2 ml_). The combined organic layers were dried (hydrophobic frit) and evaporated to give a brown oil (137 mg). This was purified by MDAP (formic acid method) to give a brown oil (104 mg). 96 mg of this racemic mixture was resolved using a Chiralpak AS column eluting with heptane: ethanol (90:10) v/v pump-mixed. Using these conditions the faster-running enantiomer 2,2,7-trifluoro-4-[(5- fluoro-3-pyridinyl)methyl]-8-[(1 S)- 1 -hydroxyethyl]-2H-1 ,4-benzoxazin-3(4H)-one (42 mg, Compound 99) and the slower-running enantiomer 2,2,7-trifluoro-4-[(5-fluoro-3- pyridinyl)methyl]-8-[(1 R)-1-hydroxyethyl]-2H-1 ,4-benzoxazin-3(4H)-one (40 mg, Compound 100) were obtained in >99% enantiomeric excess. 1H NMR (CD3OD) delta: 1.60 (3H, d), 5.32 – 5.40 (1 H, m), 7.01 (1 H, t), 7.18 – 7.25 (1 H, m), 7.57 (1 H, d), 8.38 – 8.45 (2H, m). m/z [M+H]+: 356.9 Retention time 0.85 min (LC/MS method 3). The absolute configurations were determined by ab initio vibrational circular dichroism.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256561-65-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); 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. 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Compound 2F: tert-butyl (4-(hydroxymethyl)pyridin-2-yl)carbamate Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaCl2 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight at ambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaCl (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

The synthetic route of 639091-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; RILATT, Ian; PEREZ, Michel; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; HAEUW, Jean-Francois; WO2015/162293; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 960289-03-6, 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. 960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, 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.

Preparation 21; 2-(4-Methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one; Combine 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (1.024 g, 4.42 mmol), 4-methoxyphenyl boronic acid (0.671 g, 4.42 mmol), Na2CO3 (0.94 g, 8.83 mmol), in water (10 mL), dimethoxyethane (75 mL) and CH3OH (50 mL). Purge with nitrogen for 5 min. Add Pd(PPh3 )4 (0.153 g, 0.1325 mmol) and reflux the resulting mixture overnight. Cool the reaction to RT and dilute with water (100 mL). Extract with EtOAc (3 x 100 L), and concentrate. Treat the residue with EtOAc (40 mL), collect the solid and wash with EtOAc (20 mL) and Et2O (2 x 20 mL) to give the title compound (0.950 g). Concentrate the filtrate and purify the resulting residue by chromatography to give additional product (0.140 g). The overall yield is 1.090 g (95%). MS/ES m/z 260.0[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 960289-03-6, 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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. 381247-99-0, name is Methyl 5-bromo-6-hydroxynicotinate. A new synthetic method of this compound is introduced below., SDS of cas: 381247-99-0

Methyl 5-bromo-6-oxo- 1 ,6-dthydropyridine-3-carboxylate (3.0 g, 1.0 eq) and potassium carbonate (3.6 g, 2.0 eq) were dissolved in N,N-dimethylformamide, and dropwisely added with iodomethane (1.5 eq) at room temperature. The reaction mixture was stirred at 35C for 3 hours. Upon completion of the reaction, the resultant was diluted with ethyl acetate, washed with water, dried with magnesium sulfate and filtered, and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane and crystallized with hexane to obtain a title compound (2.5 g, yield 79%).

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, 381247-99-0, Methyl 5-bromo-6-hydroxynicotinate.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; PARK, Joon Seok; YOON, Youn Jung; PARK, Chang Min; NA, Yun Soo; CHO, Min Jae; LEE, Ho Bin; HAN, Mi Ryeong; PARK, Yeon Jung; KIM, Ji Duck; WO2015/60613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 436799-33-6, 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. 436799-33-6, name is 3-Bromo-5-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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.

Example 1.1.27: (5-(trifluoromethyl)pyridin-3-yl)methanamine; 3-bromo-5-(trifluoromethyl)pyridine (1.0 g, 4.42 mmol, 1 eq) was dissolved in 20 mL anhydrous DMF. The solution was degassed by bubbling through with Ar. Zn(CN)2 (0.312 g, 2.65 mmol, 0.6 eq) and Pd(PPh3)4 were added, and the resulting solution was heated to 80 0C with stirring overnight. The reaction was cooled to room temperature and diluted with Et2O. NH4OH (28%) was added with stirring and the layers were separated. The organic layer was washed with water (x3), brine (xl), and dried over Na2SO4. The inorganics were filtered off, and the reaction mixture was concentrated in vacuo. Purification via flash chromatography on silica gel yielded 0.310 g (1.95 mmol, 44% yield) of 5- (trifluoromethyl)nicotinonitrile.

According to the analysis of related databases, 436799-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, 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: 944900-06-5, blongs to pyridine-derivatives compound. Recommanded Product: 944900-06-5

To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (115 mg, 0.549 mmol) in THF (1 mL) was added dimethylamine (823 mul, 1.65 mmol). The reaction was heated to 500C and stirred for 3 hours. The reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield the desired compound (50 mg, 0.229 mmol, 41.8 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); 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. 955372-86-8, name is 3-Bromo-5-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-Bromo-5-fluoroisonicotinic acid

TMSCHN2 (180 mL, 360 mmol, 2 equiv) was added into a solution of 3-bromo-5- fluoroisonicotinic acid (40 g, 182 mmol, 1 equiv), THF (240 mL), and MeOH (80 mL) dropwise with stirring at 0 C under nitrogen. The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/9) to afford the title compound (35 g, 83%) as yellow oil.

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, 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PARAZA PHARMA, INC.; BEAUMIER, Francis; DERY, Martin; LAROUCHE-GAUTHIER, Robin; CHEN, Huifen; SHORE, Daniel; VILLEMURE, Elisia; VOLGRAF, Matthew; HU, Baihua; LU, Aijun; CRIDLAND, Andrew; WARD, Stuart; (212 pag.)WO2018/96159; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-88-9, 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 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 15-1. 4-Iodo-N,N,3-trimethylpyridine-2-amine (Compound 15b) A DMF (7.9 mL) solution of 2-chloro-4-iodo-3-methylpyridine (Compound 15a, 500 mg, 1.97 mmol), N-ethyl-N-propan-2-ylpropane-2-amine (0.515 mL, 2.96 mmol), and a THF solution (2.96 mL, 5.92 mmol) of 2M dimethylamine was stirred at 130 C. for 17 h., then the solution was cooled to room temperature and formic acid (0.4 mL) was added. The solution was purified by reversed-phase chromatography (acetonitrile/water, 0.1% formic acid) to obtain the titled Compound 15b (258 mg, yield 50%) as a light brown solution.

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 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; YOSHINO, Hitoshi; TSUCHIYA, Satoshi; MATSUO, Atsushi; SATO, Tsutomu; NISHIMOTO, Masahiro; OGURI, Kyoko; OGAWA, Hiroko; NISHIMURA, Yoshikazu; FURUTA, Yoshiyuki; KASHIWAGI, Hirotaka; HORI, Nobuyuki; KAMON, Takuma; SHIRAISHI, Takuya; YOSHIDA, Shoshin; KAWAI, Takahiro; TANIDA, Satoshi; AOKI, Masahide; (169 pag.)US2019/225604; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-26-0, Adding some certain compound to certain chemical reactions, such as: 3430-26-0, name is 2,5-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 3430-26-0.

Step A: 5-Bromo-2-iodo-4-methyl-pyridine To a solution of 2,5-dibromo-4-methylpyridine (2 g) in acetonitrile (40 ml) at room temperature under argon were added sodium iodide (4.8 g) then acetyl chloride (0.94 g). After 3 hours stirring at room temperature the white solid formed was filtered off and the filtrate was neutralized with aqueous saturated solution of sodium hydrogenocarbonate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/cyclohexane) to afford the title product as a brown solid (2.04 g). 1H-NMR (CDCl3, 400 MHz): 8.40 (s, 1H), 7.60 (s, 1H), 2.30 (s, 3H),

According to the analysis of related databases, 3430-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem