Day: August 13, 2021

Reference of 571189-49-6 ,Some common heterocyclic compound, 571189-49-6, molecular formula is C10H16N4, 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 Compound 50 0.060 g (0.205 mmole) was added 5-(4-methylpiperazin-1-yl)pyridin- 2-amine (35.42 mg, 0.9 eq) followed by the addition of 1,4-dioxane (3 mL). After degassing with nitrogen, Pd2dba3 (12 mg), BINAP (16 mg) and sodium tert-butoxide (24 mg) were added.The contents were then heated at 90 degrees in a CEM Discovery microwave for 3 hrs. Thereaction was then loaded onto a silica gel column and purified by eluting with DCM/MeOH (0-15%). ?HNMR (600 MHz, DMSO-d6) oe ppm 0.75 (t, J7.47 Hz, 3 H) 0.91 (d, J6.73 Hz, 3 H)1.04 – 1.20 (m, 2 H) 1.80 – 1.98 (m, 1 H) 2.77 (d, J=3.81 Hz, 3 H) 2.94 – 3.90 (m, 10 H) 4.54 -4.68 (m, 1 H) 7.06 – 7.23 (m, 2 H) 7.56 – 7.75 (m, 1 H) 7.90 – 8.12 (m, 2 H) 8.29 (s, 1 H) 9.07 (s,1 H) 10.98- 11.74(m,2H). LCMS(ESI)435(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. 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; SORRENTINO, Jessica, Ann; (304 pag.)WO2016/40848; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-72-0, 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 1620-72-0, name is 2-Methyl-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-methyl-6-(trifluoromethyl)pyridine (100 mg, 0.620 mmol) was dissolved in CC14 (3 mL), and N-bromosuccinimide (NBS) (110 mg, 0.620 mmol) and 1,1′- azobis(cyclohexanecarbonitrile) (VAZO, 8 mg, 0.031 mmol) were added thereto, followed by heating and stirring at 90 C for 15 hrs. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by MPLC (Hex/EA = 5:1) to obtain the title compound as white solid (42.5 mg, yield: 28.4%). 1H NMR (300MHz, CDC13) delta 4.60 (2H, s), 7.61 (1H, d), 7.68 (1H, d), 7.90 (1H, t)

According to the analysis of related databases, 1620-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS CO., LTD.; KIM, Seon-Mi; KIM, Jae-Sun; LEE, Minhee; LEE, So-Young; LEE, Bong-Yong; SHIN, Young Ah; PARK, Euisun; LEE, Jung A; HAN, Min-Young; AHN, Jaeseung; YOO, Taekyung; KIM, Hun-Taek; WO2013/129879; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214353-79-3, Adding some certain compound to certain chemical reactions, such as: 1214353-79-3, name is Methyl 5-bromo-6-chloropicolinate,molecular formula is C7H5BrClNO2, 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 1214353-79-3.

Example 92 – Preparation of Intermediate 28 [ 00385] The synthesis of Intermediate 28 followed General Procedure 20 following. General Procedure 20 Intermediate 27 Intermediate 28 [ 00386 ] To a dry round-bottomed flask pre-cooled to 0C and under N2 gas flow, NaH (0.56 g, 14.0 mmol, 3.5 eq) was added. To this was slowly added methoxyethanol (10.0 mL) dropwise, and the mixture was stirred for 30 minutes. To this was added methyl-5-bromo-6-chloropyridine-2-carboxylate (Intermediate 27, 1.0 g, 4.0 mmol, 1.0 eq) portionwise. The reaction mixture was then stirred at ambient temperature and then heated at 100C for 10 minutes. After completion (monitored by TLC and LC-MS), the reaction mixture was concentrated under reduced pressure to obtain a brown solid residue, which was slowly quenched with acetic acid. The mixture was extracted with 10% MeOH : dichloromethane, dried over sodium sulfate and concentrated to give the desired product 5-bromo-6-(2- methoxyethoxy) pyridine-2-carboxylic acid (Intermediate 28, 0.70 g, yield-63%) m/z 278.28 [M+2]+; 1H NMR (400 MHz, DMSO) delta 13.41 (s, 1H), 8.19 (d, J = 7.8 Hz, 1H), 7.56 (d, J = 7.8 Hz, 1H), 4.52 (dd, J = 5.4, 3.8 Hz, 2H), 3.71 (dd, J = 5.4, 3.8 Hz, 2H), 3.33 (s, 3H) ppm.

According to the analysis of related databases, 1214353-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67443-38-3, 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 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-2-chloro-3-nitropyridine (5.73 g, 24.15 mmol) was dissolved in dry THF (50 ml, 610 mmol) and TEA (10.10 ml, 72.4 mmol) under nitrogen, 2-(tetrahydro-2H-pyran-4-yl)ethanamine hydrochloride (5 g, 30.2 mmol) was added and the resulting suspension stirred at RT over the weekend. The reaction mixture was poured onto ice/water (100 ml), the resulting yellow precipitate filtered off, washed with ice cold water (25 ml), dried in vacuo to give (7.49 g, 92%) as a bright yellow solid; m/z 330/332 (M+H)+(ES+);

According to the analysis of related databases, 67443-38-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; BROWN, Richard; (63 pag.)WO2016/170323; (2016); 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 953780-42-2, name is 5-Fluoro-6-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Fluoro-6-methoxynicotinic acid

To a suspension of 4-(6-(3 ,6-diazabicyclo[3. 1.1 ]heptan-3 -yl)pyridin-3 -yl)-6-(2- hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Intermediate P43, 25 mg, 0.05237 mmol) in DCM (1 mL) was added 5-Fluoro-6-methoxynicotinic acid (11.7 mg, 0.069 mmol), HATU (23.9 mg, 0.063 mmol), and DIEA (36 tL, 0.21 mmol) at ambient temperature. After stirring for two hours, the reaction mixture was concentrated in vacuo and purified using silica gel chromatography (0-20% EtOAc/MeOH as the gradient eluent) to yield the title compound (15.4 mg, 52.8% yield). ?H NIVIR (CD3OD) 8.39-8.41(d, 1H), 8.28-8.30 (m, 2H), 8.25-8.27 (d, 1H), 7.71-7.77 (m, 2H), 7.25-7.27 (d, 1H), 6.73-6.76 (d, 1H), 4.86-4.95(br.m, 1H), 4.66-4.75 (br.m, 1H), 4.18-4.29 (br.m, 1H), 3.60-3.77 (m, 3H), 2.91-2.99 (m, 1H), 1.73-1.79 (d, 1H), 1.32 (s, 6H). MS (apci) m/z = 558.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 953780-42-2.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 869557-43-7, 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.869557-43-7, name is 2-Amino-3-bromo-5-fluoropyridine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

To a 500 mL pressure flask purged with nitrogen was charged 3-bromo-5-fluoropyridin-2-amine (Compound 2a) (20 g, 104.7 mmol, 1 equiv), DABCO (17.6 g, 157.0 mmol, 1.5 equiv), and tetrabutylammonium bromide (3.38 g, 10.5 mmol, 0.1 equiv). The flask was charged with dimethyl sulfoxide (anhydrous, 40 mL) and ethyl acetate (anhydrous, 120 mL) and the resulting mixture was sparged with nitrogen for 30 min. Bis(dibenzylideneacetone) palladium (0) (3.01 g, 5.24 mmol, 0.05 equiv), a 10% w/wsolution of tri-tert-butylphosphine in hexane (21.2 g, 10.47 mmol, 0.1 equiv) and acetaldehyde (5.08 g, 115.2 mmol, 1.1 equiv) were charged and the flask was sealed. The mixture was stirred for 1 h at room temperature then heated on an oil bath at 76.5 C for 5 h. The batch was cooled and sampled for HPLC analysis. After complete conversion to Compound 3b was observed (typically 100% conversion after 5 h), the batch was quenched with water (40 mL). The aqueous phase was back extracted with ethyl acetate (40mL) and the combined organics were filtered through a celite pad to remove fine solids. The celite was rinsed with ethyl acetate (40 mL) and the resulting solution of crude product was charged with 5% Na2C03 (60 mL) and sparged with nitrogen for 30 min while mixing. The resulting organic phase was washed with water (60 mL) and concentrated at

Statistics shows that 869557-43-7 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromo-5-fluoropyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; TANOURY, Gerald, J.; NUGENT, William, Aloysius; DVORNIKOVS, Vadims; ROSE, Peter, Jamison; WO2015/73481; (2015); 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. 132606-40-7, name is 5-Bromo-2-chloro-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 132606-40-7

3-Bromo-6-chloro-2-methylpyridine (200 mg, 0.969 mmol), tert-butyl (2-oxopiperidin-4-yl)carbamate (249 mg, 1.162 mmol), Pd2(dba)3(89 mg, 0.0972 mmol), Xantphos (112 mg, 0.194 mmol), cesium carbonate (947 mg, 2.907 mmol) were stirred in dioxane (10 mL) overnight at 100C under nitrogen, cooled and concentrated to give the product after column chromatography ( 31 mg, yield 9.4%).

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, 132606-40-7, 5-Bromo-2-chloro-6-methylpyridine.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Liu Shiqiang; Zhou Yuanfeng; Liu Lei; Bao Rudi; (47 pag.)CN107793399; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 53937-02-3, 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.53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, molecular weight is 201.22, as common compound, the synthetic route is as follows.

To 4-(benzyloxy)pyridin-2(1H)-one (0.358 g, 1.779 mmol) under nitrogen was added DMF (5 mL) to produce a tan suspension. To the reaction was added NaH (60% in oil) (0.074 g, 1.860 mmol) and stirred for 1.5 hours and then 3,4-difluorobenzonitrile (0.225 g, 1.618 mmol) was added. The reaction was placed in a 90 C. oil bath for 2 hours. To the tan suspension was added 50 mL of EtOAc and the mixture washed with 4×25 mL of water, dried over MgSO4, filtered and concentrated to give 0.42 g pale yellow solids. This material was purified by flash chromatography (1-5% MeOH in CH2Cl2) to yield product (263 mg, 0.805 mmol, 50%) as a tan solid. MS (ESI) 321.2 (M+1).

Statistics shows that 53937-02-3 is playing an increasingly important role. we look forward to future research findings about 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/23702; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1480-87-1, 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. 1480-87-1, name is 2-Fluoro-3-nitropyridine, molecular formula is C5H3FN2O2, 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.

General procedure: Diethyl 2-fluoromalonate (1, 1.07 g, 6.0 mmol) in DMF (5 mL) was added dropwise to a suspension of sodium hydride (0.32 g, 8.0 mmol, 60% in mineral oil) in DMF (10 mL) and the mixture was stirred at room temperature for 20 min. Fluoroarene 2 (5.0 mmol) in DMF (10 mL) was added and the mixture was heated to 80 C. The mixture was poured into crushed ice (150 mL), acidified with conc. HCl (5 mL) and extracted with diethyl ether (3 × 30 mL). The organic phase was washed with saturated aq. NaHCO3 solution (25 mL) and saturated brine (2 × 25 mL), dried (Na2SO4) and concentrated to give the crude diester. 1H and 19F NMR analysis confirmed the formation of the intermediate aryl-fluoromalonate 3 (deltaF ~ -150 ppm) which was used in the next step without any further purification.

According to the analysis of related databases, 1480-87-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Harsanyi, Antal; Sandford, Graham; Yufit, Dmitri S.; Howard, Judith A.K.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1213 – 1219;,
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.5683-33-0, name is 2-(Dimethylamino)pyridine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.Recommanded Product: 5683-33-0

A solution of 5-tert-butyl-2-(2-hydroxyethoxy)-1-nitrobenzene (0.401 g, 1.68 mmol), di-tert-butyl dicarbonate (0.46 mL, 2.0 mmol) and dimethylaminopyridine (0.006 g, 0.05 mmol) in CH2Cl2 (15 mL) was stirred at room temp. for 30 min, at which time TLC indicated consumption of starting material. The resulting mixture was washed with water (20 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography (3% MeOH/97% CH2Cl2) to give the desired product as a yellow oil (0.291 g, 51%): 1H-NMR (DMSO-d6) ? 1.25 (s, 9H), 1.38 (s, 9H), 4.31 (br s, 4H), 7.27 (d, J=9.2 Hz, 1H) 7.64 (dd, J=2.6, 8.8 Hz, 1H) 7.77 (d,J=2.6 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5683-33-0, 2-(Dimethylamino)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Corporation; EP1449834; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem