Day: August 20, 2021

Adding a certain compound to certain chemical reactions, such as: 139042-59-4, 5-Acetyl-2-bromopyridine, 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, name: 5-Acetyl-2-bromopyridine, blongs to pyridine-derivatives compound. name: 5-Acetyl-2-bromopyridine

The mixture of compound 34-1 (25 g, 125.6 mmol), NBS (24.5 g. 138.2 mmol) and / TSA (3.4 g, 20.9 mmol) was stirred at 100 C for 2 hrs under N2. After the reaction was completed, the mixture was cooled to rt. and 200 mL of DCM was added. The organic layer were washed with water (50 mL x 3) and brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1 ) to give the title compound as yellow slurry (25 g, 71 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 279.9 [M+H] +; NMR (400 MHz, CDC13) delta (ppm): 8.95 (d, 1 H, J = 1.12 Hz), 8.1 1-8.14 (m, 1H), 7.66-7.68 (m, 1H), 4.41 (s, 2H).

The synthetic route of 139042-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; TAN, Yumei; LUO, Huichao; WO2014/19344; (2014); 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 131747-60-9, name is (2-Fluoropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6FNO

c Preparation of 2-fluoropyridine-4-carbaldehyde: A solution of 5 g (39 mmol) of (2-fluoropyridin-4-yl)methanol in dichloromethane was added dropwise to a solution of 4.6 ml (54 mmol) of oxalyl chloride and 7.6 ml (106 mmol) of dimethyl sulfoxide (DMSO) in 450 ml of dichloromethane at -78 C. and the mixture was stirred for 15 minutes. 24 ml (180 mmol) of triethylamine were then added and the reaction solution was slowly warmed to RT. It was poured onto 500 ml of water and washed once each with 10% strength citric acid (200 ml) and 10% strength sodium carbonate solution. The dichloromethane phase was dried over magnesium sulfate and concentrated under reduced pressure. Yield: 4.60 g (37 mmol), 94%.

With the rapid development of chemical substances, we look forward to future research findings about 131747-60-9.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US6358978; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 159451-66-8, Adding some certain compound to certain chemical reactions, such as: 159451-66-8, name is N-Boc-2-Amino-5-bromopyridine,molecular formula is C10H13BrN2O2, 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 159451-66-8.

(VI) Scheme VI: Intermediate 41: tert-butyl (5-(1-((1s,4s)-4-hydroxycyclohexyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)pyridin-2-yl)carbamate Under the protection of nitrogen, 0.218 g (0.8 mmol) of tert-butyl 2-carbamate -5-bromopyridine (Intermediate 38), 0.244 g (0.96 mmol) of bis(pinacolato)diboron, 0.234 g (2.4 mmol) of potassium acetate and 0.052 g (0.064 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride were suspended in 15 ml of dioxane, and heated at 100 C for 2 h. The reaction was monitored by TLC. After the reaction was completed, the crude reaction solution was cooled to room temperature, added with 0.2 g (0.54 mmol) of Intermediate 40, 0.9 g (2.7 mmol) of cesium carbonate, 10 ml of dioxane, 10 ml of 2M sodium carbonate solution and 0.044 g (0.054 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride, and heated at 110 C for 5 h. The reaction was monitored by TLC. After the reaction was completed, most of dioxane was removed from the reaction solution, and the residue was added with water and extracted with dichloromethane. The organic phases were combined, dried, and rotary evaporated to dryness to afford a crude product. The crude product was purified by preparative silica gel plate (dichloromethane/methanol =10/1, V/V) to afford a product (240 mg) as a reddish brown solid. Yield: 90.9%.

According to the analysis of related databases, 159451-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Forelandpharma Co. Ltd.; ZHANG, Xingmin; JI, Qi; WANG, Lei; GAO, Congmin; WANG, Ensi; DU, Zhenjian; GONG, Longlong; CHEN, Bo; (137 pag.)EP3072893; (2016); 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. 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H7Br2NO

a) Preparation of Intermediate 24; A mixture of 2-bromo-1-(4-pyridinyl)-ethanone, hydrobromide (0.02 mol) and (5-chloro-2,4-dimethoxyphenyl)-thiourea (0.02 mol) in EtOH (200 ml) was stirred and refluxed for 4 hours, then cooled to room temperature. The resulting precipitate was filtered off, washed with EtOH and dried, yielding 6.0 g (60%) of intermediate 24 as a hydrobromide salt (.HBr).

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, 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; Thuring, Johannes Wilhelmus John F.; MacDonald, Gregor James; Grantham, Christopher James; Dinklo, Theodorus; Lesage, Anne Simone Josephine; US2011/269748; (2011); 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.100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine, molecular formula is C6H6BrN3O2, molecular weight is 232.04, as common compound, the synthetic route is as follows.name: 2-Amino-5-bromo-4-methyl-3-nitropyridine

This reaction was conducted under inert gas protection. The reaction vessel was first charged with 2000 ml methanol and cooled to about 0 C. with slight agitation. Then 9.1 kg acetyl chloride was added. The exothermic reaction was then cooled and agitated for 10 minutes. The next addition was 100 g 2-amino-5-bromo-3-nitro-4-picoline (the compound of formula 2 at 0 C. Then 236.5 g of t-butyl nitrite was added at a rate such that the temperature did not exceed 5 C. The slight evolution of nitrogen gas was noted. After the completion of the reaction, cooling was removed and the reaction mixture within the vessel was allowed to warm to 25 C. in about 30 minutes. The mixture was agitated at 25 C. for about 3-4 hours. After 4-5 hours a clear solution was obtained. Reaction completeness was monitored by HPLC after about 4 hours. The reaction was complete after about 5 hours. The reaction mixture was concentrated in vacuo to about 1000 mL. Then 500 ml of water was added and the product precipitated. Then 250 ml saturated sodium bicarbonate solution was added with good agitation to neutralize the HCl and dissolve the hydroxy impurity. The mixture was agitated at 20-25 C. for about 15 minutes and then the precipitate was collected and washed with 1000 ml of water. The product was then dried at 40 C. in vacuo. Yield was 75.0 g. Analytical data: m.p. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (DMSO-d6) (delta, ppm): 2.31 (s, 3H), 3.96 (s, 3H), 8.55 (s, 1H): 13C-NMR (DMSO-d6) (delta, ppm): 17.49, 54.91, 99.41, 114.39, 141.02, 149.23, 153.46; HRMS calcd for C7H7BrN2O3 245.96401 found (M+1): 246.97184; Elemental Analysis: calcd for C7H7BrN2O3: C 34.03, H 2.85, N 11.34; found: C 33.81, H 2.91, N 11.24.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Liu, Wansheng; Patel, Sunil S.; Cuniere, Nicolas; Lear, Yvonne; Deshpande, Prashant P.; Simon, Jeffrey N.; Lai, Chiajen; Pullockaran, Annie J.; Soundararajan, Nachimuthu; Bien, Jeffrey T.; US2007/32503; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 934266-82-7, 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.934266-82-7, name is 5-Bromothiazolo[5,4-b]pyridin-2-amine, molecular formula is C6H4BrN3S, molecular weight is 230.09, as common compound, the synthetic route is as follows.

Step 2: tert-Butyl 5-bromothiazolo[5,4-b]pyridin-2-ylcarbamate To a suspension of 5-bromothiazolo[5,4-b]pyridin-2-amine (15.0 g, 65.1 mmol) in DCM (300 mL) was added di-tert butyl dicarbonate (21.0 g, 96.2 mmol) and 4-dimethylaminopyridine (8 g, 65.5 mmol). The reaction mixture stirred at room temperature for 2 h and evaporated in vacuo. The residue was purified via flash chromatography on silica gel (solvent gradient: 0-50% ethyl acetate in petroleum ether) to yield 13 g (60%) of the title compound as a white solid. LCMS (ESI): [M+H]+=330/332.

Statistics shows that 934266-82-7 is playing an increasingly important role. we look forward to future research findings about 5-Bromothiazolo[5,4-b]pyridin-2-amine.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-03-8 ,Some common heterocyclic compound, 884495-03-8, molecular formula is C5H4BrFN2, 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: 3-Amino-5-fluoro-pyridine-2-carboxyilic acid methyl ester: [00308] A solution of 3-amino-2-bromo-5-fluoropyridine (CAS: 884495-03-8, 955 mg, 5 mmol) and Pd(dppf)Cl2?CH2Cl2 (204 mg, 25 mmol) in dry MeOH (15 mL) and DIEA (1.74 mL, 10 mmol) was flushed with N2 after which a pressure of 8 atm CO was applied. The reaction was heated at 70 C. After completion, the mixture was diluted with water and extracted with EtOAc. The combined organic fractions were washed with NH4Cl solution, dried over Na2SO4, filtered and concentrated. The obtained residue was purified by column chromatography eluted using a mixture of EtOAc and petroleum ether (25:75). The obtained titled compound was used as such.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-03-8, its application will become more common.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7584-05-6, 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 7584-05-6, name is 3-Methylisonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-methylisonicotinonitrile (26, 168 mg, 1.4 mmol)in DMF (3 mL) was added 1,1-dimethoxyl-N,N-dimethylmethanamine(400 muL, 2.8 mmol). The mixture was heated to reflux overnight. Thenthe mixture was cooled to RT and additional 200 muL of 1,1-dimethoxyl-N,N-dimethylmethanamine was added to the mixture. The mixture washeated to reflux overnight. Then repeated addition of 200 muL 1,1-dimethoxyl-N,N-dimethylmethanamine to the mixture. The mixture washeated to reflux overnight. After completion of the reaction, the mixturewas cooled to RT and concentrated in vacuo to give a brown oil,the residue was purified by flash column chromatography on silica(EtOAc/Petroleum ether 1:2) to yield the yellow solid (20%). 1H NMR(400 MHz, CDCl3) delta 8.69 (s, 1H), 8.14-8.11 (m, 1H), 7.25-7.23 (m,1H), 7.16 (d, J=13.6 Hz, 1H), 5.21 (d, J=13.6 Hz, 1H), 2.95 (s, 6H).

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 7584-05-6, 3-Methylisonicotinonitrile.

Reference:
Article; Qin, Li-Huai; Wang, Zhi-Long; Xie, Xin; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3559 – 3572;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1822-51-1, 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 1822-51-1 as follows.

Example 62: 6-(Pyridin-4-yl-methyl)-naphthalene-1-carboxylic acid (4-fluoro-3-trifluoromethyl- phenvD-amide; A mixture of 22.4 mg (0.10 mMol) Pd(O2CCH3)2) 52.6 mg (0.20 mMol) triphenylphosphine, 151 mg (0.33 mMol) 6-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-naphthalene-1- carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide and 229.3 mg (1.08 mMol) K3PO4 in 3 ml toluene is degassed repeatedly by evaporation and flushing with N2. Then 59 mg (0.36 mMol) 4-chloromethyl-pyridine hydrochloride are added and the mixture is stirred at 80 0C for 20 h, when additional 18.5 mg (0.082 mMol) Pd(O2CCH3)2 and 43.1 mg (0.164 mMol) triphenylphosphine are added. After 3 h at 110 0C the reaction mixture is poured into water and EtOAc. The aqueous phase is separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography [Combi Flash; CH2CI2 ? CH2CI2/(Me0H + 10 % NH3aq) 9:1] gives the title compound: MS: [M+1]+ = 425; HPLC: AtRe( = 12.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1822-51-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/59234; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1173081-96-3, Adding some certain compound to certain chemical reactions, such as: 1173081-96-3, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride,molecular formula is C8H13ClN2O, 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 1173081-96-3.

N-((4,6-dimethyl-2-oxo-l,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H- pyran-4-yl)amino)-4-methyl-4 ‘-(morpholinomethyl)- [1,1 ‘-biphenyl] -3-carboxamide (Compound I)A mixture of 5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methyl-4’- (morpho linomethyl)-[ 1,1 ‘-biphenyl] -3 -carboxylic acid (540 g, 1.23 mol) and 3-(aminomethyl)- 4,6-dimethyl-dihydro-pyridin-2(lH)-one hydrochloride (279 g, 1.48 mol) was suspended in DMSO (2.70 L) and treated with triethylamine (223 ml, 1.60 mol). The mixture was stirred at 25 C for 30 min and treated with EDC-HC1 (354 g, 1.85 mol) and HOBT hydrate (283 g, 1.85 mol). The reaction mixture was stirred at rt for 16 h. After addition of triethylamine (292 ml, 2.09 mol), the mixture was cooled to 15 C, diluted with water (10.1 L) maintaining the temperature below 30 C, and stirred at 19-25 C for 4 h. The resulting precipitate was filtered, washed twice with water (2.70 L), and dried under vacuum to give a crude product (695 g, wt-wt analysis = 78%). For the further purification of the product, recrystallization was conducted. A crude product (20.00 g, 34.92 mmol) was suspended in a mixture of ethanol (190 ml) and water (10.00 ml) and heated to 75C until a clear solution was obtained. The solution was allowed to cool to rt overnight. The precipitate was filtered, washed twice with a mixture of ethanol (30.0 ml) and water (30.0 ml), and dried under vacuum at 35 C to give the title compound as an off white solid (14.0 g, 70% recovery from the crude and 90%> yield based on wt-wt assay).

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. 1173081-96-3, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; EISAI R&D MANAGEMENT CO., LTD.; KUNTZ, Kevin W.; CHOI, Hyeong-wook; MATHIEU, Steven; SANDERS, Kristen; CHANDA, Arani; WO2015/57859; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem