Tag: M.W:200-300

Application of 171366-19-1 , The common heterocyclic compound, 171366-19-1, name is (2-Fluoro-4-iodopyridin-3-yl)methanol, molecular formula is C6H5FINO, 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.

[00344] 3-(((tert-Butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridineTo a solution of (2-fluoro-4-iodopyridin-3-yl)methanol (3.52 g, 13.91 mmol) in CH2CI2 (80 mL) at room temperature was sequentially added imidazole (1.894 g, 27.8 mmol) and TBDMS-C1 (2.52 g, 16,69 mmol). The reaction was stirred at room temperature for 1 h before diethylether was added and the insoluble salts were filtered. Silica gel was added to the filtrate prior to the solvent removal under vacuum. The dry silica gel was packed, and the adsorbed product was purified by flash chromatography (hexane/EtOAc 10:0 to 7:3) to give 3-(((ieri-butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridine as a white solid (4.5 g). LC/MS m/z 368 [M+H]+.

The synthetic route of 171366-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
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. 98027-84-0, name is 2,6-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, 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

Preparative Example 2,6-Dichloro-4-cyclopropylpyridine Cyclopropylzinc bromide (0.5 M in tetrahydrofuran, 15 mL, 7.3 mmol) was added to a mixture of 2,6-dichloro-4-iodopyridine (1.0 g, 3.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (211 mg, 0.182 mmol) in anhydrous tetrahydrofuran (10 mL) at 0 C. After being stirred at room temperature for 4 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate = 100: 1) to provide 2,6- dichloro-4-cyclopropylpyridine. MS ESI calc’d. for C8H8C12N [M + H]+ 188, found 188. XH NMR: (400 MHz, CDC13) 5 6.89 (s, 2H), 1.87 – 1.80 (m, 1 H), 1.18 – 1.13 (m, 2H), 0.84 – 0.80 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 98027-84-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7169-97-3, 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 7169-97-3, name is N-(5-Bromopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows.

N-(5-bromopyridin-2-yl)acetamide (4.30 g, 20 mmol),P-carboxyphenylboronic acid(3.66 g, 22 mmol) was added to a 250 ml pear-shaped bottle.Further, cesium carbonate (13.0 g, 40 mmol) and tetrakistriphenylphosphine palladium (1.2 g, 1 mmol) were successively added.Add acetonitrile/water to the above mixture (V:V=3:2)200ml. N2 protection, the oil bath was heated to 90 C for 48 h. After the reaction,The reaction solution was cooled to room temperature and suction filtered.The filtrate was adjusted to pH 4 with 6 mol/L hydrochloric acid, and a white solid was precipitated.The filter cake was vacuum dried to give the product 3.89 g, yield 76%.

According to the analysis of related databases, 7169-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (14 pag.)CN109651243; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, 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, COA of Formula: C13H13NO3, blongs to pyridine-derivatives compound. COA of Formula: C13H13NO3

A. Synthesis of [5-(benzyloxy)-4-isopropoxypyridin-2-yl]methanol (C32). A solution of 5-(benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one (prepared by a procedure similar to that reported by M. M. O’Malley et al., Organic Letters 2006, 8, 2651-2652) (1.3 g, 5.6 mmol) in N,N-dimethylformamide (11.2 mL) was treated with 2-iodopropane (95%, 1.77 mL, 16.8 mmol) and potassium carbonate (1.17 g, 8.42 mmol). The slurry was stirred for 2.5 hours at room temperature and then heated at 80 C. for 18 hours, with addition of 2-iodopropane (1.3 mL, 12 mmol) after the first hour. The mixture was extracted three times with ethyl acetate, and the combined organic layers were dried over sodium sulfate. Filtration and removal of solvent in vacuo gave a residue, which was purified by silica gel chromatography (Eluants: 0%, then 20%, then 40% 2-propanol in ethyl acetate) to provide the product as a brown solid. Yield: 700 mg, 2.56 mmol, 46%. 1H NMR (400 MHz, DMSO-d6) delta 8.06 (s, 1H), 7.30-7.44 (m, 5H), 7.06 (s, 1H), 5.28 (t, J=5.9 Hz, 1H), 5.13 (s, 2H), 4.72 (septet, J=6.0 Hz, 1H), 4.42 (d, J=5.9 Hz, 2H), 1.32 (d, J=6.0 Hz, 6H).

The synthetic route of 59281-14-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; Brodney, Michael Aaron; Efremov, Ivan Viktorovich; Helal, Christopher John; O’Neill, Brian Thomas; US2013/150376; (2013); 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.1446237-40-6, name is 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one, molecular formula is C7H7BrN2O3, molecular weight is 247.05, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a stirred mixture of NEUCI (17.3 g, 323.42 mmol, 10.0 equiv) in EEO/EtOH (1 /1 , 400 ml_) was added 5-bromo-1 , 4-dimethyl-3-nitro-1 , 2-dihydropyridin-2-one (8.0 g, 32.38 mmol, 1 .0 equiv) and Fe (18.1 g, 324.1 1 mmol, 10.0 equiv) at room temperature. The mixture was stirred at rt. for 2 hours, the solid was filtered off. The filtrate was diluted with water (100 ml_) and extracted with ethyl acetate (200 ml_ x 2). The organic layers were combined and washed with saturated NaCI (aq.), dried over with anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 6.56 g (93%) 3-amino-5-bromo-1 ,4-dimethyl- pyridin-2(1 H)-one as a red solid that was used directly without further purification. LCMS (ESI) m/z: [M+H]+ = 217.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1446237-40-6, 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ZHOU, Qianhe; BOCKER, Michael; MILLAN, David, Simon; CHAN, Ho, Man; SOARES, Luis; NETHERTON, Matthew, Russell; RUPPEL, Sabine, K.; YANG, Zhaoxia; LOWE, Jason, T.; BRUCELLE, Francois; (220 pag.)WO2019/152440; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 888721-65-1, 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. 888721-65-1, name is 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of 1- (4-fluorophenyl) -6-methyl-2-oxo-l, 2- dihydropyridine-3-carboxylic acid (56.7 mg, 0.229 mmol) and N- [ 6- (4-amino-2-fluorophenoxy) -3-methylimidazo [1, 2-a] pyridin-2- yl] cyclopropanecarboxamide (60 mg, 0.176 mmol) in N, N- dimethylformamide (1 mL) were added N, N-diisopropylethylamine (61 muL, 0.352 mmol) and HATU (87 mg, 0.229 mmol), and the mixture was stirred at room temperature for 17 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate alone) to give a yellow oil. The obtained oil was dissolved in ethyl acetate (1 mL) and left standing at room temperature for 17 hr. The precipitated solid was collected by filtration, washed with diethyl ether and collected by filtration to give the title compound (76 mg, 75%) as a white solid.1H-NMR (DMSOd6, 300 MHz) delta 0.78 (4H, m) , 1.74 – 1.91 (IH, m) , 2.07 (3H, s), 2.26 (3H, s) , 6.61 – 6.79 (IH, m) , 7.01 – 7.15 (2H, m) , 7.28 – 7.37 (IH, m) , 7.38 – 7.54 (5H, m) , 7.97 (IH, dd, J = 13.2, 2.5 Hz), 8.19 (IH, d, J = 1.9 Hz), 8.48 (1 H, d, J = 7.6 Hz), 10.21 (IH, br s) , 11.97 (IH, s) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,888721-65-1, 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/136663; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-86-7 , The common heterocyclic compound, 153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, 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.

(S)-5-(3-Bromophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (243 mg, 0.599 mmol) obtained in Step 1 of Example 13 was dissolved in 1,4-dioxane (7 mL), and the mixture was stirred at 100C for 2 hours after adding bis(pinacolato)diboron (0.380 g, 1.50 mol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 98.0 mg, 0.120 mmol), and potassium acetate (0.295 g, 3.00 mmol). The reaction mixture was filtered through sellite, and the filtrate was diluted withy ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography. The resulting crude product was dissolved in 1,4-dioxane/water = 4/1 (12.5 mL), and the mixture was stirred at 100C for 3 hours after adding 2-chloro-4-iodopyridine (216 mg, 0.902 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 49.0 mg, 0.060 mmol), and sodium carbonate (191 mg, 1.80 mmol). The reaction mixture was then filtered through sellite, and the filtrate was extracted with ethyl acetate. The organic layer was then washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give 5-[3-(2-chloropyridin-4-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro5,8,10,10b-tetraazabenzo[e]azulen-6-one (113 mg, 43% (2 steps)). ESI-MS: m/z 438 [M + H]+. 1H NMR (CDCl3) delta(ppm) : 1.70 (m, 1H), 1.94 (m, 1H), 2.10 (m, 1H), 2.25 (m, 1H), 2.56 (s, 3H), 3.82-3.95 (m, 4H), 4.40 (m, 1H), 7.35 (dt, J = 2.02, 7.33 Hz, 1H), 7.43 (dd, J = 1.65, 5.31 Hz, 1H), 7.51-7.59 (m, 4H), 8.44 (d, J = 5.32 Hz, 1H), 8.87 (s, 1H).

The synthetic route of 153034-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59237-53-5, Methyl 6-chloro-5-nitronicotinate, 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, HPLC of Formula: C7H5ClN2O4, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5ClN2O4

a Methyl 6-methylamino-5-nitro-nicotinate 1.6 g (7.4 mMol) of methyl 6-chloro-5-nitro-nicotinate (see Bernie et al. in J. Chem. Soc. 1951, 2590) were stirred in 20 ml of 40percent aqueous methylamine solution at room temperature for 30 minutes. The reaction mixture was then diluted with ice water, the yellow precipitate formed was filtered off and dried. Yield: 1.2 g (80percent of theory), Rf value: 0.66 (silica gel; ethyl acetate/ethanol/glacial acetic acid=90:5:5)

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6087380; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

A mixture of 2-bromo-3,5-dichloropyridine (5.672 g, 25 mmol), sodium iodide (11241.7 mg, 75 mmol) and chlorotrimethylsilane (2716 mg, 25 mmol) in MeCN (50 mL) was heated under reflux for 45 min. The reaction mixture was then poured into a 2.0 M aqueous solution of sodium hydroxide (10 mL) and extracted with diethyl ether (20 mL x 3). The combined organic layers were washed with brine and evaporated to afford crude product, which was purified by biotage (EtOAc/PE=l% ~ 10%, ISCO 40 g, 25 mL/min, normal phase silica gel, uv 254) to afford the target compound 3,5- dichloro-2-iodopyridine (3800 mg, 55.5 % yield) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.35 (t, J= 4.5 Hz, 1H), 8.01 (d, J= 2.3 Hz, 1H). GC-MS m/z calcd for [C5H2C12IN]: 272.9; found: 273.0.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 5-Bromo-2-chloro-3-pyridinamine [commercially available] (10 g, 48.2 mmol) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.46 ml, 96 mmol) added, and the mixture stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at room temperature for 5 h. A further portion of methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at room temperature overnight. The pH was adjusted to ?pH6 by the addition of 2M hydrochloric acid. The mixture was then extracted with dichloromethane (2*150 ml) the combined organic layers were dried using a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M sodium hydroxide (50 ml) added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and extracted with dichloromethane (150 ml). The aqueous layer was then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid (13.45 g).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem