Tag: M.W:200-300

Synthetic Route of 885500-55-0, Adding some certain compound to certain chemical reactions, such as: 885500-55-0, name is Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate,molecular formula is C10H9ClN2O2, 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 885500-55-0.

Preparation Example 5; To ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.00 g) was added DMF (20 ml), and the mixture was ice-cooled. Sodium hydride (60% dispersed in mineral oil) (427 mg) was added thereto, followed by stirring for 1 hour under ice-cooling. Thereafter, [2-(chloromethoxy)ethyl](trimethyl)silane (1.71 mL) was added dropwise thereto, followed by warming to room temperature and stirring for 30 minutes. After completion of the reaction, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/Hx =0/100 to 10/90) to obtain ethyl 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.50 g) as a colorless transparent oily material.

According to the analysis of related databases, 885500-55-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP2420502; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15862-30-3, 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. 15862-30-3, name is 3-Bromo-5-nitropyridine, molecular formula is C5H3BrN2O2, 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.

Step 1 To a solution of 3-bromo-5-nitropyridine (XCV) (295 mg, 1.45 mmol) in dioxane (14 mL) was added 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (XCVI) (420 muL, 1.89 mmol), PdCl2(dppf)2, (120 mg, 0.15 mmol) and 2M aqueous K3PO4 (2.2 mL, 4.36 mmol). The reaction was microwaved at 90 C. for 2 h. The reaction was cooled and the organic phase was separated, dried over MgSO4 and evaporated under vacuum. The residue was purified by silica gel column chromatography (100% hexane?6:94 EtOAc:hexane) to give 3-benzyl-5-nitropyridine (XCVII) as brown oil (117 mg, 0.54 mmol, 37% yield). 1H NMR (DMSO-d6) delta ppm 4.16 (s, 2H), 7.21-7.25 (m, 1H), 7.31-7.33 (m, 4H), 8.45-8.46 (m, 1H), 8.93 (d, J=2 Hz, 1H), 9.21 (d, J=3 Hz, 1H); ESIMS found for C12H10N2O2 m/z 215.0 (M+H).

According to the analysis of related databases, 15862-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Mak, Chi Ching; Bollu, Venkataiah; Eastman, Brian; US2015/266825; (2015); A1;,
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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. 1108724-32-8, name is 3-Bromo-5-(1,1-difluoroethyl)pyridine. A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-5-(1,1-difluoroethyl)pyridine

Add benzophenone imine (215 mg, 1.19 mmol), cesium carbonate (640 mg, 1.96 mmol), (±)-2,2′-bis(diphenylphosphino)-l, -binaphthalene (BINAP, 98 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 90 mg, 0.098 mmol] to the solution of 3-bromo-5-(l, 1 -difluoroethyl)pyridine (200 mg, 0.9 mmol) in dioxane (10 mL), stir the resulting mixture under nitrogen atmosphere at 100C for 16 hrs. Cool the reaction mixture to room temperature, filter off the solid, concentrate the filtrate under reduced pressure, purify by flash chromatography (silica gel, EtOAc_PE=2:l) to yield the title compound (296 mg, 92%). MS: (M+l): 323.

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, 1108724-32-8, 3-Bromo-5-(1,1-difluoroethyl)pyridine.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1001413-01-9 ,Some common heterocyclic compound, 1001413-01-9, molecular formula is C13H9F2NO3, 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.

Thiophene-2-methanamine (0.562 g, 0.00496 mol; Acros) and l-(3,4-difluoro-benzyl)- 2-oxo-l,2-dihydro-pytauidine-3-carboxylic acid (1.32 g, 0.00496 mol) and N,N,N,N’-tetramethyl- O-(7-azabenzotriazol-l-yl)uronium hexafluorophosphate (2.08 g, 0.00546 mol; Applied Biosystems) was dissolved in N,N-dimethylformamide (15.0 mL, Acros). To this was added N,N-diisopropylethylamine (4.32 mL, 0.0248 mol; Acros) and the reaction was stirred overnight at room temperature. The reaction was evaporated to dryness, then partitioned between 5% citric acid, ethyl acetate. The organic layer was washed with saturated sodium chloride, dried with sodium sulfate, filtered and concentrated. The residue was purified on preparative HPLC. Appropriate fractions were combined and evaporated to give the product in 1.04 g yield. MS m/z= 361.06 M+H.

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. 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC.; WO2008/5457; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 78607-36-0 , The common heterocyclic compound, 78607-36-0, name is 2-Chloro-3-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.

To a flame-dried flask were added Pd(PPh3)4 (10 mol %), Xantphos (10 mol %), Cs2CO3 (3 eq) and 2-chloro-3-iodopyridine (1.2 eq). Then, 1NB (1 eq) and DMF (0.15 M) were added to the reaction mixture under an N2 atmosphere. The reaction mixture was stirred for 10 min at room temperature, and then heated at 140 C. in a pre-heated oil bath for 24 h. After that, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through a short pad of Celite, and washed with CH2Cl2. The combined organic extracts were concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to provide the product DFE-1NB-2 in 42% yield.

The synthetic route of 78607-36-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Zhu, Zhi-Qiang; (232 pag.)US2018/337345; (2018); 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 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Safety of tert-Butyl (6-chloropyridin-3-yl)carbamate

1,1-Dimethylethyl (6-Chloro-4-iodo-3-pyridinyl)carbamate n-Butyllithium (1.6M in hexanes, 22 mL, 35 mmol) was added dropwise to a stirred, cooled (-78 C.) solution of 1,1-dimethylethyl (6-chloro-3-pyridinyl)carbamate (Description 6, 2.68 g, 11.7 mmol) and N,N,N’,N’-tetramethylethylenediamine (5.3 mL, 4.1 g, 35 mmol) in ether (60 mL). The mixture was allowed to warm to -10 C. and stirred for 2 h. The mixture was cooled to -78 C. and a cooled (-10 C.) solution of iodine (6.0 g, 24 mmol) in ether (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 18 h. Saturated aqueous ammonium chloride was added and the mixture was extracted with ether. The combined organic fractions were washed with aqueous sodium metabisulfite (10%), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as a brown solid (2.3 g, 55%). 1H NMR (400 MHz, CDCl3) delta 8.94 (1H, s), 7.73 (1H, s), 6.64 (1H, br s), and 1.54 (9H, s).

With the rapid development of chemical substances, we look forward to future research findings about 171178-45-3.

Reference:
Patent; Dinnell, Kevin; Elliott, Jason Matthew; Hollingworth, Gregory John; Shaw, Duncan Edward; US2002/22624; (2002); A1;,
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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, 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. Product Details of 15862-37-0

A 150 mL pressure flask was charged with (6-chloro-2-methoxypyridin-3- yl)boronic acid (2.5 g, 13.3 mmol) and 2,5-dibromo-3-nitropyridine (3.38 g, 12.01 mmol). The solids were suspended in THF (60 mL). The mixture was treated with PdCl2(dppf)-CH2Cl2 adduct (0.545 g, 0.667 mmol) and K3P04 (2M, 20 mL, 40 mmol). Argon was bubbled through the mixture for 5 min while sonicating. The flask was capped and heated to 80C in a preheated oil bath. The reaction was cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to remove THF. The remaining water layer was diluted further with water and was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered and concentrated under vacuum to give a solid. The material was taken up in DCM and a minimum of ethyl acetate and purified by flash column chromatography (80g ISCO column, 0-30% ethyl acetate/hexanes over 600 mL, then 50-100% over 300 mL). Like fractions were concentrated to give 4.5g (78%). NMR (400MHz, CDCh) delta 8.94 (d, J=2.0 Hz, 1H), 8.44 (d, J=2.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 3.89 (s, 3H). LC/MS (M+H) = 345.95

With the rapid development of chemical substances, we look forward to future research findings about 15862-37-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54916-66-4, 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 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

As shown in step 4(b)-i of Scheme 4(b), HATU (8.194 g, 2.55 mmol) and DIPEA (5.570g, 7.507 mL, 43.10 mmol) was added to a solution of 5-bromo-2-methoxypyridine-3- carboxylic acid (5 g, 21.55 mmol) in DMF (50 mL). The resulting solution was stirred for 10 minutes followed by the addition of ethanamine hydrochloric acid (1.757 g, 2.196 mL, 21.55 mmol). The resulting solution was stirred at room temperature for 5 hours. To the reaction mixture was added water (100 mL) and ethyl acetate (100 mL). The organic layer was separated and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-2% methanol in dichloromethane gradient) to produce 5-bromo-N-ethyl-2-methoxynicotinamide as off white solid (Compound 2015, 3.4g): 1H NMR (DMSO-d6) delta 8.41 (d, J = 2.5 Hz, 1H), 8.31 (s, 1H), 8.20-8.13 (m, 1H), 3.95 (s, 3H), 3.35-3.23 (m, 2H), 1.11 (t, J = 7.2 Hz, 3H).

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (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. 1312784-89-6, name is tert-Butyl 1-methyl-6,7-dihydro-1H-imidazo[4,5-c]pyridine-5(4H)-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 1312784-89-6

Under nitrogen protection, dissolve 5.0Kg of 1-methyl-6,7-dihydro-1H-imidazo [4,5-C] pyridine-5- (4H) -carboxylic acid tert-butyl ester in 30L of tetrahydrofuran and stir, The temperature of the dry ice ethanol bath is reduced to -60 ,Slowly add 16.9L n-butyl lithium n-hexane solution (2.5mol / L),Control the reaction temperature not to exceed -50 C, keep the temperature at -50 C ~ -60 C for 1 hour after the addition is completed, pass in 2.8 kg of dried carbon dioxide gas, keep the temperature not to exceed -40 C, and increase the temperature to 20 after completion Reaction at -25 C for 2 hours; add 1mol / L dilute hydrochloric acid aqueous solution to adjust PH = 2-3, stir for 10 minutes, separate layers, extract the aqueous layer with 80L ethyl acetate, combine the organic layers, wash with 30L saturated brine, without Dry over sodium sulfate, filter and concentrate to give an oily liquid 1-methyl-6,7-dihydro-1H-imidazo [4,5-C] pyridine-5- (4H) -carboxylic acid tert-butyl ester-2- Carboxylic acid 5.2Kg, purity by HPLC detection was 98.2%, yield was 87.7%.

The synthetic route of 1312784-89-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Gao Jian; Yu Jurong; (8 pag.)CN110950886; (2020); A;,
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 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

A colorless mixture of A-13 (900.0 mg, 3.34 mmol) in H2504 (50%,10.0 mL) was stirred at 120 C for 3 hours. The mixture was diluted with ice-water, neutralizedwith solid Na2CO3 to pH = 7, and extracted with DCM (50 mL x 2). The combined organiclayers were washed with brine (10 mL), dried over Na2504, filtered and concentrated to affordA-14 (550.00 mg, 2.79 mmol) as an oil. ?H NMR (400 MHz, CDC13) oe11 8.38 – 8.32 (m, 1H),7.95 (d, 1H), 7.72 (d, 1H), 6.83 (dd, 1H), 6.47 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 885276-93-7.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem