Day: May 27, 2021

Application of 1018949-67-1, 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 1018949-67-1 as follows.

General procedure: In a three neck round bottom flask (50 mL in volume) along with guard tube was charged with carboxylic acid (1.0 equiv) in 5 ml solvent combination of CH2Cl2: DMF (4:1). After few minutes stirring at room temperature the resulting suspension was cooled with an ice-water bath prior to the addition of the bis(2-oxo-3-oxazolidinyl)phosphonic chloride (1.5 equiv) and the starting compound 1a (1.0 equiv). The resulting mixture was stirred again for few minutes and then DIPEA (3.0 equiv) was added. The mixture was kept at 0 C for 30-60 min and then stirred at room temperature until the starting material was consumed as monitored by TLC analysis. Ice-water (20 mL) was added while maintaining vigorous stirring. In the cases when the indole precipitated upon addition of water, the solid was filtered off and dissolved in EtOAc (20 mL). In all other cases, the aqueous layer was extracted with EtOAc (3 × 20 mL). The extracts were combined and washed with water (2 × 50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified either by silica gel chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018949-67-1, its application will become more common.

Reference:
Article; Jadhav, Jagannath; Khanapaure, Sharanabasappa; Kurane, Rajanikant; Salunkhe, Rajashri; Rashinkar, Gajanan; Tetrahedron Letters; vol. 54; 50; (2013); p. 6858 – 6863;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74420-15-8, Adding some certain compound to certain chemical reactions, such as: 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 74420-15-8.

Example 79 Synthesis of (2-Ethoxy-naphthalen-1-yl)-[3-(4-methanesulfonyl-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-methanone 84 Step 1-Preparation of (3-Bromo-pyrrolo[2,3-b]pyridin-1-yl)-(2-ethoxy-naphthalen-1-yl)-methanone 85 3-Bromo-7-azaindole (500 mg, 2.0 mmol) 3 was dissolved in N,N-dimethylformamide (50 mL) and sodium hydride (210 mg, 5.3 mmol, 60% dispersion in mineral oil) and 2-Ethoxy-naphthalene-1-carbonyl chloride (710 mg, 3.0 mmol) were added. The reaction mixture was stirred at ambient temperature for 30 min, cast into ice water (100 mL) and extracted into ethyl acetate. The organic portion was dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated. Purification via column chromatography (10% Ethyl acetate in hexanes) provided the desired product 85 (800 mg, 80%).

According to the analysis of related databases, 74420-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ibrahim, Prabha N.; Bremer, Ryan; Gillette, Sam; Cho, Hanna; Nespi, Marika; Mamo, Shumeye; Zhang, Chao; Artis, Dean R.; Lee, Byunghun; Zuckerman, Rebecca; US2006/100218; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1678-53-1 ,Some common heterocyclic compound, 1678-53-1, molecular formula is C6H6N2O2, 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.

General procedure: To a stirred mixture of 1.00 mmol of nitropicoline 35 or 63, 1.20 mmol of the appropriate benzaldehyde, and 1.5 mmol of Huenig’s base in THF (7 mL/g of nitropicoline 35/63) was added 1.3 mmol of a 1 M THF solution of TBAF. The resulting mixture was heated 60 C for 1.5e2.0 h in the case of 2,3-dihydrofuro[3,2-c] pyridines or for 18 h in the case of 2,3-dihydrofuro[2,3-b]pyridines. After cooling to room temperature, the reactions were quenched with sat. aqueous NH4Cl. The solution was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography as specified above.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1678-53-1, its application will become more common.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130115-85-4, 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. 130115-85-4, name is 5-Bromo-6-chloropyridin-3-ol, molecular formula is C5H3BrClNO, 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.

To a solution of diethyl azodicarboxylate (1.89 mL, 12.0 mmol) in THF (30 mL) was added triphenylphosphine (3.15 g, 12.0 mmol) at 0C, and the reaction mixture was stirred for 0.5 hour. 1-BOC-(S)-pyrrolidinemethanol (2.41 g, 12.0 mmol) and 5-bromo-6-chloropyridine-3-ol (2.09 g, 10.0 mmol) were then added. The reaction mixture was allowed to warm to room temperature overnight. The solvent was removed, and the residue was chromatographed on a silica gel column, eluting with EtOAc/hexane (1:5 and 1:2) to afford an oil (3.80 g, 97%). MS (CI/NH3) m/z 391,393 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) delta 1.65-2.05 (m, 4H), 3.20-3.35 (m, 2H), 3.95-4.15 (m, 3H), 7.98 (d, J = 2.9 Hz, 1H), 8.21 (d, J = 2.9 Hz, 1H).

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 130115-85-4, 5-Bromo-6-chloropyridin-3-ol.

Reference:
Patent; Abbott Laboratories; EP1047690; (2004); B1;,
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.139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.Product Details of 139022-25-6

(5-(([2 ‘-Bipyridin]-3-yloxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (product of step-2, 0.320 g, 0.997 mmol) was reacted with imidazo[l,2- a]pyridine-6-carboxylic acid (0.193 g,1.197 mmol) in presence of BOP reagent (0.485 g, 1.096 mmol) and DIPEA (0.525 mL, 2.991 mmol ) in DMF (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulphate and concentrated under reduced pressure to get a residue. The residue was purified by combiflash column chromatography (dichloromethane/methanol/triethylamine = 91/8/1) to afford the title compound (0.150 g, 35%) as a solid. LCMS: nt/z 428.7 [M+H] +; HPLC: 97.93 % ; NMR (400 MHz, DMSO-de): delta 9.16 – 9.12 (d, / = 1.8 Hz, 1H), 9.11 (s, 1H), 9.05 – 8.99 (t, / = 5.5, 5.5 Hz, 1H), 8.61 – 8.54 (dt, / = 3.3, 1.5, 1.5 Hz, 1H), 8.37 – 8.31 (d, / = 4.5 Hz, 1H), 8.30 – 8.25 (m, 1H), 8.11 (s, 1H), 7.68 – 7.60 (m, 4H), 7.51 – 7.45 (dd, / = 7.9, 4.8 Hz, 1H), 7.45 – 7.39 (dd, / = 8.4, 4.6 Hz, 1H), 5.01 – 4.91 (dq, / = 10.4, 5.6, 5.6, 5.4 Hz, 1H), 4.28 – 4.12 (m, 4H), 3.27 – 3.15 (dd, / = 17.6, 11.2 Hz, 1H), 3.00 – 2.86 (dd, / = 17.7, 7.1 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 128372-89-4, 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. 128372-89-4, name is tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H15NO3, 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: A dried Schlenk flask was charged with arylboronic acid (3, 0.4 mmol), [Rh(L1)(OH)]2 (L1=(S,S)-Ph-thpe, 3.8 mg, 0.005 mmol), KHF2 (3.2 mg, 0.04 mmol), and 1 mL of anhydrous toluene under argon. The resulting mixture was stirred at room temperature for 30 min. 1-N-Boc-2-oxo-5,6-dihydropyridine (2c, 39.4 mg, 0.2 mmol) in toluene (1 mL) was added. Seven minutes later, 0.1 mL of isopropanol was added. After being stirred at room temperature for 2 h, the reaction was quenched with saturated aq NH4Cl, extracted with ethyl acetate (20 mL×3), and the combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel (300-400 mesh) column chromatography to afford 4.

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 128372-89-4, tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Article; He, Zhi-Tao; Wei, Ya-Bing; Yu, Hong-Jie; Sun, Cai-Yun; Feng, Chen-Guo; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 68; 45; (2012); p. 9186 – 9191;,
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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H8N2O

To a stirring suspension of (6-aminopyridin-3-yl)methanol (1 .24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0mmol) in EtOH (10 mL) at room temperature was added cone sulfuric acid (1 0.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6- (hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1 H NMR (400MHz, c/6-DMSO) delta 9.16 (d, J = 6.8 Hz, 1 H), 8.26 (s, 1 H), 7.67 (s, 1 H), 7.19 (dd, J = 1 .6, 6.8 Hz, 1 H), 5.57 (t, J = 6.4 Hz, 1 H), 4.63 (d, J = 6.0, 2H), 4.36 (q, J = 7.2 Hz, 2H), 1 .35 (t, J = 6.8 Hz, 3H). MS m/z 221 .1 (M+1 ) +.

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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; IRM LLC; LOREN, Jon; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; RUCKER, Paul Vincent; WO2013/33203; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 133427-08-4, 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.133427-08-4, name is Imidazo[1,2-a]pyridine-8-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.

Step E: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).To a solution of imidazo[l,2-alpha]pyridine-8-carboxylic acid (36.6 mg, 226 mumol), l-(2,4- difluorophenethyl)piperazine hydrochloride (45.0 mg, 150 mumol) and triethylamine (210 mul, 1504 mumol) in DMF (0.75 mL) was added 1-propylphosphonic acid anhydride solution (50% in ethyl acetate, 183 muL, 0.301 mmol). The mixture was stirred for 2 h, quenched with water and purified by preparative HPLC/MS. The resultant lyophilate was dissolved in DCM, treated with MP-carbonate resin (-200 mg). The mixture was stirred for 30 min and filtered to remove the resin. The solvent was removed under reduced pressure to afford the title compound as a white solid (33.0 mg).

Statistics shows that 133427-08-4 is playing an increasingly important role. we look forward to future research findings about Imidazo[1,2-a]pyridine-8-carboxylic acid.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
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. 147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 147149-98-2

POCl3 (98.85 mg, 0.65 mmol) was added to a mixture of 1-(2-methylimidazo[1,2-a]pyridin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (100 mg, 0.32 mmol), 2-(trifluoromethyl)pyridin-4-amine (52.26 mg, 0.32 mmol), pyridine (127.49 mg, 1.61 mmol) in CH2Cl2 (3 mL) at rt. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with 20 mL sat. K2CO3 aq, and extracted with CH2Cl2 (20 mL*3). The organic layer was separated and concentrated under reduced pressure. It was purified by preparative high-performance liquid chromatography (35% to 65% (v/v) CH3CN and H2O with 0.05% ammonia hydroxide). The pure fractions were collected and the organic solvent was concentrated under reduced pressure. The aqueous layer was lyophilized to dryness to give the desired product as a white solid. (80 mg, purity: 99.5%, yield: 54.3%). LCMS (ESI) m/z M+1: 454.9. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.32 (s, 3H), 7.08 (s, 1H), 7.32 (d, J=7.06 Hz, 1H), 7.41 (dd, J=9.04, 7.28 Hz, 1H), 7.75 (d, J=9.04 Hz, 1H), 7.94 (dd, J=5.73, 1.76 Hz, 1H), 8.21 (d, J=1.76 Hz, 1H), 8.65 (s, 1H), 8.69 (d, J=5.29 Hz, 1H), 11.29 (s, 1H).

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, 147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]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, Product Details of 1206979-33-0, blongs to pyridine-derivatives compound. Product Details of 1206979-33-0

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate (530 mg, 1.33 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (203 mg, 1.33mmol) in 1,4-dioxane (30 mL) was added Cul (101 mg, 0.53 mmol), N1,N2-dimethylethane-1,2-diamine (94 mg, 1.06 mmol), and K2CO3 (734 mg, 5.32 mmol). The mixture was heated at 100C, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using petroleumether:EtOAc (3:1~1:1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate as yellow solid. (446 mg, 71%). MS (ESI) m/z: 473 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem