Day: August 10, 2021

Adding a certain compound to certain chemical reactions, such as: 138116-34-4, (4-Aminopyridin-3-yl)methanol, 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 138116-34-4, blongs to pyridine-derivatives compound. Product Details of 138116-34-4

General procedure: To a solution of 2-aminobenzyl alcohol (1.0 mmol, 1.00 equiv) and MnO2 (3.0 equiv.) in dry CH2Cl2 (20 mL) were stirred for 18 h at room temperature. The completion of reaction was monitored by TLC analysis. After the completion of reaction solvent was evaporated under reduced pressure at 40C and taken up for next step without any purification. 50 mL of methanol was added to same round bottom flask and corresponding aryl amines (1.0 equiv.), isocyanides (1.0 equiv.) and pTSA (15 mol%) added sequentially and the reaction mixture was stirred at room temperature for 12-15h. After the completion of reaction (monitored by TLC), the solvent of reaction mixture was evaporated under reduced pressure at 45oC to afford a black residue which was purified by column chromatography on silica gel (230-400 mesh) by eluting with gradient solution of hexane/EtOAc to get pure compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138116-34-4, (4-Aminopyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Dev, Kapil; Ramakrishna; Maurya, Saransh Wales; Siddiqui, Ibadur Rahman; Kant, Ruchir; Maurya, Rakesh; Tetrahedron Letters; vol. 58; 12; (2017); p. 1202 – 1206;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67754-03-4, 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.67754-03-4, name is Methyl 2,5-dichloronicotinate, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.

Description 85: methyl 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1- yl)nicotinate (D85)To a cooled (0C) solution of tert-butyl 3-((2,4-difluorophenyl)amino)azetidine-1 – carboxylate (D31 ) (90 mg, 0.316 mmol) in dichloromethane, a mixture of trifluoroacetic acid/dichloromethane (3ml/1 ml) was added and the reaction mixture was stirred 1 h. The solvents were evaporated in vacuo and the residue was dissolved in tetrahydrofuran/methanol (3/1 ml) triethylamine (0.132 ml, 0.95 mmol) was added followed by the addition of methyl 2,5-dichloronicotinate (52.33 mg, 0.253 mmol) and the resulting mixture was stirred 1 2h at 75 C. The residue abtained after solvent evaporation was purified by Biotage SNAP-Si column eluting with cyclohexane/ethyl acetate from 100/0 to 90/10. Collected fractions afforded the title compound (D85) (0022/086/5) (38 mg).MS: (ES/+) m/z: 354.1 [MH+] C16H14CIF2N302 requires 353.07.1 H NMR (400MHz ,CHLOROFORM-d) delta = 8.26 (d, J = 2.4 Hz, 1 H), 8.00 (d, J = 2.4 Hz, 1 H), 6.89 – 6.71 (m, 2 H), 6.47 (dt, J = 5.1 , 9.2 Hz, 1 H), 4.50 (dd, J = 7.3, 9.3 Hz, 2 H), 4.33 (br. s., 1 H), 4.12 (br. s., 1 H), 3.98 – 3.85 (m, 5 H)

Statistics shows that 67754-03-4 is playing an increasingly important role. we look forward to future research findings about Methyl 2,5-dichloronicotinate.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-49-9, 2-Chloro-5-fluoro-4-iodopyridine, 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, name: 2-Chloro-5-fluoro-4-iodopyridine, blongs to pyridine-derivatives compound. name: 2-Chloro-5-fluoro-4-iodopyridine

General procedure: A reaction vial was charged with a mixture of the appropriate halide (1 equiv.), the organoboron reagent (1-3 equiv.), a Pd catalyst (0.05-0.1 equiv.) and an inorganic base (2-5 equiv.) in a mixture of water and 1 ,4-dioxane or toluene, as stated. The mixture was de gassed by evacuating and refilling with N2 three times or by bubbling N2 through for 5-15 min, then the reaction tube was sealed. The reaction was heated under the indicated conditions for the indicated time and allowed to cool to rt. Water or saturated NH4CI(aq) was added and the resulting mixture was extracted using DCM (x 3). The combined organic extracts were dried (phase separator), concentrated under reduced pressure and the remaining residue was purified by flash chromatography to give the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-49-9, 2-Chloro-5-fluoro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); 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.136117-70-9, name is Imidazo[1,2-a]pyridine-8-carbonitrile, molecular formula is C8H5N3, molecular weight is 143.1454, as common compound, the synthetic route is as follows.Product Details of 136117-70-9

Synthesis of 3-iodoimidazo [1 ,2-a]pyridine-8 -carbonitrile. To a stuffed solution of imidazo[1,2-a]pyridine-8-carbonitrile (1.2 g, 8.38 mmol) in dichloromethane (10 mL) was added N-iodosuccinimide (1.89 g, 8.38 mmol). LCMS monitored the reaction until the starting material consumed completely. The reaction mixture was dilutedwith dichloromethane and water. The separated organic layer was dried sodium sulfate, filtered and concentrated to give 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile (1.8 g, 6.69 mmol, 80 % yield) as a brown solid. MS (ES+) C8H81N3 requires: 269, found: 270 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136117-70-9, Imidazo[1,2-a]pyridine-8-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7 , The common heterocyclic compound, 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

At room temperature, 400 ml of N,N-dimethylformamide was added to a 1 L three-necked flask to start stirring. Add 5_bromo-7-azaindole (30g, 0.15mol) and potassium tert-butoxide (25·6g, 0 · 23mol) to the reaction flask. After stirring and clearing, cool the ice bath to wait for the internal temperature. At 0 C, triisopropylsilyl chloride (43.3 g, 0.225 mol) diluted with 80 ml of tetrahydrofuran was initially added dropwise. After the addition is completed, the reaction is maintained at 0-5 C for 10-20 minutes. TLC control, the reaction is over. 300 ml of water was added to the reaction flask, and the mixture was stirred for 15 minutes. The aqueous phase was extracted with methyl tert-butyl ether (200 ml*2). The organic phase was combined and the organic phase was washed with 500 ml of saturated aqueous sodium chloride solution once. After drying over anhydrous sodium sulfate, the solvent is concentrated to obtain an oil, and 50 ml of methanol is added to precipitate a solid. The solid is vacuum filtered and dried to obtain a compound of the formula. Yield: 50.5 g, yield: 93.8%.

The synthetic route of 183208-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Zhuang Yinqiang; Peng Shaoping; Jiang Hui; (11 pag.)CN107434807; (2017); A;,
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. 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl (6-chloropyridin-3-yl)carbamate

tert-Butyl(6-chloro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)pyridin-3- yl)carbamate. BuLi(2.166 mL, 5.70 mmol) was added to the diethyl ether (17 mL) solution of TMEDA(0.706 mL, 4.68 mmol) and tert-butyl (6-chloropyridin-3- yl)carbamate (0.4653g, 2.035 mmol) at -78 C. The reaction was stirred at this temperature for 1hour. Dihydro-2H-pyran-4(3H)-one (0.230 mL, 2.442 mmol) wasadded to the reaction mixture (at this moment, the bath temperature was -75C).The reaction was stirred for 2.5 hours before quenched with NH4CI (sat.). Thereaction was diluted with ethyl acetate and washed with water three times. Theorganic layer was separated, dried (Na2SC”4), filtered and concentrated.Flash column eluted with ethyl acetate in hexane from 0 to 25% to 50%> gavethe desired product (0.3600g, 45% yield, 83% pure). MS(ES+) m/e 329 [M+H]+.

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, 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-14-9, 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. 84487-14-9, name is 2-Bromo-3-nitropyridine-4-amine. A new synthetic method of this compound is introduced below.

To a solution of N1-(3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)-N2,N2-dimethylethane-1,2-diamine (CVII) (2.00 g, 6.49 mmol, 1.2 eq), 2-bromo-3- nitropyridin-4-amine (CVIII) (1.18 g, 5.41 mmol, 1.0 eq), Na2C03 (1.15 g, 10.82 mmol, 2.0 eq) and Pd(dppf)Cl2 (395.73 mg, 540.83 muiotaetaomicron, 0.1 eq) in dioxane (40 mL) and H20 (8 mL) was degassed and then heated to 80C overnight under N2. TLC (PE:EtOAc=l : l) showed the starting material was consumed completely. The reaction mixture was poured into H20 (300 mL). The mixture was extracted with EtOAc (3 x 250 mL). The organic phase was washed with saturated brine (300 mL), dried over anhydrous MgSO i, concentrated in vacuum to give a residue, which was purified by silica gel column chromatography (PE/EtOAc=5/l) to afford N1-(3-(4-amino-3- nitropyridin-2-yl)-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CIX) (1.50 g, 4.70 mmol, 86.9% yield) as a solid. ESIMS found for C15H18FN5O2 m/z 320.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,84487-14-9, 2-Bromo-3-nitropyridine-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., SDS of cas: 126325-47-1

A solution of 6-bromo-2-methylpyridin-3-amine (24 g, 128 mmol) and AcOH (14.7 mL 257 mmol) in MeOH (200 mL) was cooled to 0C, Br2 (36.9 g, 230.9 mmol, 11.9 mL) was added and stirred at 0C for 5 hours. The mixture was quenched with saturated aqueous Na2S03 (500 mL), extracted with ethyl acetate (300 mL x 3). The organic layer was washed with brine (200 mL), dried over Na2S04, and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ethenethyl acetate = 2:1) to afford 4,6-dibromo-2-methylpyridin-3-amine.

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, 126325-47-1, 6-Bromo-2-methylpyridin-3-amine.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; MARIGO, Mauro; (142 pag.)WO2019/121840; (2019); 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. 89570-82-1, name is 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

A CEM-designed 10-mL pressure-rated vial was charged with POCl3(2 mL), 3-chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine (211 mg,1mmol), 4-methoxylbenzoic acid or analogous acid (1mmol). The mixture was irradiated in a CEM Discover Focused Synthesiser (150 W, 140C, 200 psi, 15min). The mixture was cooled to room temperature by passing compressed air through the microwave cavity for 2 min. It was poured into cold ice (40 mL) and the formed precipitate filtered. The crude solid was recrystallised from EtOH to give the title compound 2a and others. All the other compounds were synthesised according to the same procedure.

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, 89570-82-1, 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine.

Reference:
Article; Yang, Ming-Yan; Zhai, Zhi-Wen; Sun, Zhao-Hui; Yu, Shu-Jing; Liu, Xing-Hai; Weng, Jian-Quan; Tan, Cheng-Xia; Zhao, Wei-Guang; Journal of Chemical Research; vol. 39; 9; (2015); p. 521 – 523;,
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. 882500-21-2, name is 5-Bromo-6-trifluoromethylpyridin-2-ylamine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrF3N2

A mixture of 5-bromo-6-(trifluoromethyl)pyridin-2-amine (3.0 g, 12.3 mmol), Zn(CN)2 (0.81 g, 6.9 mmol), Pd2(dba)3 (0.57 g, 0.6 mmol), and Xantphos (0.72 g, 1.2 mmol) in DMA (12 mL) was placed in a sealed tube. The mixture was degassed with argon and stirred at 160C for 20h. The mixture was poured into water and extracted with EtOAc (2x). The combined organic layers were dried over magnesium sulfate and concentrated to dryness. The residue was purified by column chromatography on silica gel eluting with 3: 1 EtOAc/hexanes to afford 1.9 g of 6-amino-2-(trifluoromethyl)nicotinonitrile as a solid. lR NMR (400 MHz, CDC13) delta 7.74 (d, 1H), 6.67 (d, 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, 882500-21-2, 5-Bromo-6-trifluoromethylpyridin-2-ylamine.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem