Day: June 29, 2021

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.118399-86-3, name is 6-Bromo-2-methylpyridin-3-ol, molecular formula is C6H6BrNO, molecular weight is 188.0219, as common compound, the synthetic route is as follows.Product Details of 118399-86-3

To a 50 mL round bottom flask equipped with a stir bar was added 6-bromo-2- methylpyridin-3 -l (250 mg, 1.330 mmol), 2-(4-fluorophenyl)ethan- 1-01(186 mg, 1.330 mmol), triphenylphosphine (418 mg, 1.596 mmol) and THF (10 mL). To the stirred solutionwas added DIAD (0.310 mL, 1.596 mmol). The solution warmed to a mild reflux, then cooled within 5 minutes. The solution was stirred at r.t. for 2 hrs. The reaction solution was concentrated in vacuo and the resulting oil was diluted with a mm of acetone, then concentrated onto Celite in vacuo. The resulting powder was subjected to silica gel chromatography(40 g column, 5-40% EtOAc:Hex) to afford the product 6-bromo-3-(4-fluorophenethoxy)-2-methylpyridine (386 mg, 1.244 mmol, 94 % yield) as a white solid.?H NMR (500 MI-Tz, chloroform-d) 7.29 – 7.21 (m, 3H), 7.03 (t, J=8.7 Hz, 2H), 6.95 (d, J=8.5 Hz, 1H), 4.14 (t, J=6.6 Hz, 2H), 3.11 (t, J=6.5 Hz, 2H), 2.42 (s, 3H). ESI-MS(+) m/z = 309.9 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,118399-86-3, 6-Bromo-2-methylpyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74784-70-6, 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 74784-70-6 as follows.

Step A: 3-nitro-5-(trifluoromethyl) pyridin-2-amine To a solution of 5~(trifluoromethyl)pyridine-2-amine (l.lg, 6.79mmol) dissolved in sulfuric acid (2OmL) at room temperature was added nitric acid (0.475 g, 6.79mmol). After heating to 700C for Ihr, the reaction mixture was cooled to room temperature and diluted with EtOAc and ice. The organic layer was separated, washed with sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound (680 mg). LC/MS: m/z 208(M+H). 1H-NMR (500MHz, CD3OD): delta 8.60 (d, 1H), 8.67 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74784-70-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/152072; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86873-60-1, 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.86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

General procedure for the preparation of amides of formula 1.4:A solution of the carboxylic acid (0.23 mmol) in methanol (5 ml) was cooled to 0 C. 4- (4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmophiholinium chloride hydrate (DMTMM) (80 mg, 0.27 mmol) was added and the solution was stirred at 0 C for 30 minutes. Thereafter, a solution of the intermediate diamine B7 (0.21 mmol) in methanol (5 ml) was added dropwise at 0 C via syringe. The reaction mixture was stirred at 23 C for 18-60 hours. For the workup, the reaction mixture was poured into a solution of sodium carbonate (1M) followed by the extraction with ethyl acetate. The organic layer was separated, washed with brine and dried over sodium sulphate. Removal of the solvent at reduced pressure left a residue which was purified by chromatography on silica gel or on a silica-NH2 phase using a mixture of dichloromethane and methanol (0-10%) to give the pure amides of formula I.Example 33(R)-N-(2′-Amino-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[l,3]oxazine]-6-yl)-5- chloropicolinamideThe condensation of (R)-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[l,3]oxazine]-2′,6-diamine (intermediate B7.1) and 5-chloropicolinic acid yielded the title compound (56% yield) as a white solid. MS (ISP): m/z = 409.2 [M+H]+..

The chemical industry reduces the impact on the environment during synthesis 86873-60-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; NARQUIZIAN, Robert; PINARD, Emmanuel; WOSTL, Wolfgang; WO2012/163790; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5470-18-8, 2-Chloro-3-nitropyridine, 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, 5470-18-8, blongs to pyridine-derivatives compound. Safety of 2-Chloro-3-nitropyridine

17. Preparation of 2-Hydrazino-3-nitropyridine 2-Chloro-3-nitropyridine (100 g, 0.63 mol), hydrazine monohydrate (70.4 mL, 72.6 g, 1.45 mol) and methanol (1.3 L) were mixed and heated to reflux with stirring. After 30 min the reaction mixture was cooled and filtered collecting the insoluble materials. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained as well as the insoluble materials from the filtration were diluted with water. The insoluble solids present were collected by filtration, washed with water, and dried to obtain 95.2 g (98 percent of theory) of the title compound as a bright yellow powder melting at 168-169 C. Elemental Analysis C5 H6 N4 O2 Calc.: %C, 39.0; %H, 3.90; %N, 36.4; %S, 8.27 Found: %C, 39.1; %H, 4.17; %N, 36.1; %S, 8.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-18-8, its application will become more common.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
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. 120800-05-7, name is 1-(5,6-Dichloropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Safety of 1-(5,6-Dichloropyridin-3-yl)ethanone

To a 50-mL round-bottomed flask was added l-(5,6-dichloro-3- pyridinyl)ethanone (700 mg, 3.68 mmol), cesium fluoride (28 mg, 0.18 mmol, Sigma- Aldrich, St. Louis, MO), and DME (8 mL). The reaction mixture was cooled to 0 C and under a nitrogen atmosphere (trifluoromethyl)trimethylsilane (0.65 mL, 4.42 mmol, Sigma-Aldrich, St. Louis, MO) was added. The reaction mixture was stirred at 0 C for 1.5 h and then carefully quenched by adding aqueous 5N HC1 (5 mL). The reaction mixture was stirred at room temperature for 18h. The reaction mixture was carefully diluted with saturated aqueous sodium bicarbonate (about 10 mL) and extracted with EtOAc (2 x 30 mL). The organic extract was washed with brine, dried (Na2S04), filtered, and concentrated in vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a silica gel column (40 g), eluting with a gradient of 0 % to 10% EtOAc in hexanes, to provide 2-(5,6-dichloro-3-pyridinyl)- 1,1,1 – trifluoro-2-propanol (812 mg) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.60 (d, J= 2.15 Hz, 1H), 8.27 (d, J = 2.15 Hz, 1H), 7.12 (s, 1H), 1.75 (s, 3H). (m/z (ESI, +ve ion) 260.0 (M)+.

The synthetic route of 120800-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, 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, Safety of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, blongs to pyridine-derivatives compound. Safety of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

To a solution of sulfurisocyanatidic chloride (25 mg, 0.18 mmol) in DCM (2 mL) was added a solution of Intermediate GW-14.3 (60 mg, 0.18 mmol) and TEA (0.040 mL, 0.27 mmol) in DCM (2 mL) in an ice-water bath and the reaction mixture was stirred for 20 min. Then a solution of 2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (32 mg, 0.27 mmol) in DCM (2 mL) was added, followed by TEA (0.07 mL, 0.5 mmol) and the reaction mixture was stirred for 2 min, the bath was removed and the stirring was continued at rt for 2 h. The reaction mixture was was concentrated and the residue was redissolved in methanol and purified by preparative HPLC to afford the title compound (13.7 mg). LC-MS retention time = 3.53 min; m/z = 565.10 [M+H]+. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 muiotaeta particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1261269-66-2, 2,4,6-Trichloronicotinaldehyde, 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, 1261269-66-2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2Cl3NO

Ethylhydrazine (2.16 g, 14.39 mmol, 1.00 equiv) was added to a solution of2,4,6-trichloropyridine-3-carbaldehyde (3 g, 14.26 mmol, 1.00 equiv) and triethylamine (4.3 g,42.49 mmol, 3.00 equiv) in ethanol (100 mL) at -78C under nitrogen. The resulting solution was stilTed for 3 hours at 0 C. After completion the reaction was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:20) to give the title compound (800 mg, 26%) as a white solid. LC-MS (ES, m/z): 216 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1261269-66-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6602-32-0, 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. 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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 3; MeI, K2CO3 NaOMe DMF DMF M 3-2 3.3 3-5 2:62-bromo-3 -hvdroxv-6-iodopvridine (3 -2)To a solution of 2-bromo-3 -hydroxy pyridine (3A., 28 g, 161 mmol) in water (360 mL) was added K2CO3 (44.5 g, 322 mmol) and I2 (40.8 g, 161 mmol). The system was stirred for 1.5h at ambient temperature, cooled to 00C and then treated with concentrated HCl until solids precipitated from solution (pH~ 6.0). The solids were isolated by filtration and dried to give the title compound Q1Z) as a brown solid. ESI+ MS C5H3BrINO: 299.8 found, 299.9 required.

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 6602-32-0, 2-Bromo-3-hydroxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGMAN, Jeffrey, M.; COLEMAN, Paul, J.; MATTERN, Mamio Christa; MERCER, Swati, P.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2010/51236; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74115-13-2, Adding some certain compound to certain chemical reactions, such as: 74115-13-2, name is 5-Bromo-3-pyridinol,molecular formula is C5H4BrNO, 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 74115-13-2.

To a solution of NaOH (2.40 g, 1 15 mmol) in water (96mL) was added 5- bromopyridin-3-ol (10. Og, 57.5 mmol), followed by NaOCI aq. solution (60 ml of 10% solution). The reaction mixture was stirred at rt for 16 hours and then quenched with acetic acid (7 ml). The precipitate was isolated by filtration and washed with water (200 mL). After drying under high vacuum, 7.0 g of product was obtained (59%). 1H NMR (400 MHz, DMSO d6): 1 1 .36 (s, 1 H), 8.01 (d, J = 2.1 Hz, 1 H), 7.50 (d, J = 2.2 Hz, 1 H).

According to the analysis of related databases, 74115-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FU, Jiping; JIN, Xianming; LEE, Patrick; LU, Peichao; YOUNG, Joseph Michael; (76 pag.)WO2018/47109; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 777899-57-7 ,Some common heterocyclic compound, 777899-57-7, molecular formula is C7H5ClN2O4, 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.

Intermediate 27A: Methyl 2-(1 ,4-diazabicvclo[3.2.2lnonan-4-yl)-5-nitroisonicotinateTo a solution of methyl 2-chloro-5-nitroisonicotinate (Intermediate 26A) (0.1 g, 0.46 mmol) in methanol (3 mL) under nitrogen was added 1 ,4-diazabicyclo[3.2.2]nonane (0.18 g, 0.55 mmol) and triethylamine (7 mg, 0.69 mmol), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 10g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-(1 ,4-diazabicyclo[3.2.2]nonan-4-yl)-5- nitroisonicotinate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,777899-57-7, its application will become more common.

Reference:
Patent; N.V. ORGANON; RATCLIFFE, Paul David; CLARKSON, Thomas Russell; JEREMIAH, Fiona; MACLEAN, John Kinnaird Ferguson; WO2011/45258; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem