Category: pyridine-derivatives

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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below., Quality Control of (4-Chlorophenyl)(pyridin-2-yl)methanone

General procedure: Bioconversion was conducted with 20 mM 1a-10a,20 U·mL-1KpADH variants, 40 mM isopropanol in PBS buffer (pH 7.0,100 mM) in total volume of 2 mL at 30 C and 180 rpm overnight. Then,1 mL of the reaction mixture was withdrawn and extracted with ethylacetate. The organic phase was isolated by centrifugation and driedover anhydrous MgSO4. The conversion rate and enantioselectivity ofthe products were analyzed as described in supporting information.

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, 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone.

Reference:
Article; Wang, Yue; Dai, Wei; Liu, Yongmei; Zhang, Zhongwei; Zhou, Jieyu; Xu, Guochao; Ni, Ye; Catalysis Communications; vol. 108; (2018); p. 1 – 6;,
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.128071-77-2, name is 4-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, molecular weight is 204, as common compound, the synthetic route is as follows.Safety of 4-Bromo-2-fluoronicotinaldehyde

To a solution of ethyl prop-2-ynoate (2.92 g, 29.8 mmol) in THF (100 mL) at -78 C under N2was added LDA (14.9 mL of a 2M solution in THF/heptane/ethylbenzene, 29.8 mmol) dropwise. The mixture was stirred at -78 C for 20 minutes and a solution of 4-bromo-2-fluoro-pyridine-3-carbaldehyde (5.79 g, 28.38 mmol) in THF was added. The mixture was stirred at -78 C for 1 h and the reaction was quenched by the addition of saturated aqueous NH4C1 (100 mL). The mixture was extracted with EtOAc (3 x 100 mL) and the combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound (1.47 g, 4.87 mmol, 17% yield) as a red oil. LCMS m/z = 302.0 [M+Hf ?H NMR (400 MHz, CDC13):oe ppm 1.32 (t, J = 7.2 Hz, 3 H), 3.08 (dd, J = 9.2, 2.8 Hz, 1H), 4.26 (q, J = 7.2 Hz, 2H), 6.04 (dd, J =9.1, 1.9 Hz, 1H), 7.49-7.44 (m, 1H), 8.05 (dd, J = 5.3, 0.8 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,128071-77-2, 4-Bromo-2-fluoronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; REN, Albert S.; SCHRADER, Thomas O.; KASEM, Michelle; ZHU, Xiuwen; (182 pag.)WO2018/35477; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884495-01-6, 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 884495-01-6, name is 4-Bromo-5-fluoro-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-2-ethoxy-5-fluoro-pyridine 0.20 g (1.04 mmol) 4-bromo-5-fluoro-pyridin-2-ol, 0.83 mL (10.4 mmol) ethyliodide and 0.43 g (1.56 mmol) Ag2CO3 are added to 5 mL DCM and stirred at r.t. over night. The reaction is quenched by the addition of water. DCM is added, the resulting mixture is filtered and the organic layer is separted, dried over MgSO4, filtered again and the solvent is removed in vacuo. C7H7BrFNO (M=220.0 g/mol) ESI-MS: 220/222 [M+H]+Rt(HPLC):1.27 min (method B)

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 884495-01-6, 4-Bromo-5-fluoro-2-hydroxypyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-21-5, 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. 3430-21-5, name is 5-Bromo-3-methylpyridin-2-amine, molecular formula is C6H7BrN2, 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.

Sodium nitrite (5.0 g, 72.5 mmol) in water (10 mL) was added dropwise to a cooled (0 C) mixture of 2-amino-5-bromo-3-methylpyridine (5.0 g, 26.7 mmol; Lancaster) in 2.6 M sulfuric acid (70 mL). The mixture was allowed to warm to ambient temperature, stir for 1.5 hours, filtered, and the filtercake was washed with cold water and air dried. The precipitate was dissolved in dichloromethane (100 mL), dried (MgSO4), and concentrated to provide the title compound as a solid (4.2 g, 84%). MS (DCI/NH3) m/z 348 (M+H)+.

According to the analysis of related databases, 3430-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; EP1428824; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-61-8, 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. 1122-61-8, name is 4-Nitropyridine, molecular formula is C5H4N2O2, 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.

Weigh accurately 122.5mg of [(p-cymene) RuCl2] 2 and 62.5mg of bpy,Put in a reaction container and mix, and add 10 mL of methanol solution to dissolve the mixture.The reaction was refluxed for 4 h. After the reaction solution was cooled, 10 mL of an AgNO3 (136 mg) aqueous solution was added.Stir overnight at room temperature and filter to obtain the filtrate.To the filtrate was added 5-fold equivalents of 4-nitropyridine, and the reaction was refluxed for 5 h. The above reactions were all performed under the protection of N2.The reaction solution was spin-dried to obtain the crude product as a yellow solid.Separation and purification using a silica gel column. The eluent is a mixture of acetonitrile CH3CN, water H2O, and saturated potassium nitrate KNO3 aqueous solution, and the volume ratio is CH3CN: H2O: KNO3 = 50: 5: 1;The obtained solid was dissolved with a small amount of water, and a saturated aqueous ammonium hexafluorophosphate solution was added to obtain a yellow precipitate.Filtration, the precipitate was washed with a small amount of water, then with a small amount of ether, and dried under vacuum to obtain complex 3. After weighing, calculateThe yield is 36%.

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 1122-61-8, 4-Nitropyridine.

Reference:
Patent; Chongqing Medical University; Chen Yongjie; Liu Shan; Zhao Hua; Ren Jialu; Wang Qian; Du Hui; (13 pag.)CN110256502; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-06-6, 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.886365-06-6, name is Methyl 5-bromo-4-methylpicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.

Intermediate Example Int15.17.045-bromo-4-methylpyridine-2-carboxylic acid To a stirred solution of Int15.17.03 (1 .0 g) in THF (20 mL), methanol (5 mL) and water (5 mL) was added an aqueous solution of lithium hydroxide (6.1 mL; c = 1M). The mixture was stirred at r.t. for 1 h. Aqueous hydrochloric acid was added, until pH 4 was reached. The mixture was extracted with chloroform using a continous liquid /liquid extractor (from Normag Labor- und Prozesstechnik GmbH, llmenau, Germany) for 16 h. The solvent was removed in vacuum to give 870 mg of the title compound.

Statistics shows that 886365-06-6 is playing an increasingly important role. we look forward to future research findings about Methyl 5-bromo-4-methylpicolinate.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54231-34-4, 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.54231-34-4, name is 3-Iodo-2-nitropyridine, molecular formula is C5H3IN2O2, molecular weight is 249.99, as common compound, the synthetic route is as follows.

A mixture of 3-iodo-2-nitropyridine (2 g, 8 mmol), (4-chlorophenyl)boronic acid (1.5 g, 9.6 mmol), Na2CO3 (1.7 g, 16 mmol) and Pd(PPh3)4(277 mg, 0.24 mmol) in dioxane (20 mL) and water (10 mL) was degassed with nitrogen, heated to 110 C. and stirred for 18 hours under nitrogen atmosphere. The reaction was cooled to r.t, filtered and concentrated in vacuo. The residue was diluted with water, extracted with EA. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Petroleum ether/EtOAc=3:1) to give 3-(4-chlorophenyl)-2-nitropyridine (1.4 g, 75% yield) as a yellow solid. LC/MS (ESI, m/z): [M+1]+=234.6.

Statistics shows that 54231-34-4 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-2-nitropyridine.

Reference:
Patent; Kymera Therapeutics, Inc.; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (180 pag.)US2020/10468; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (177 mg, 480 mumol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 24-1 (100.0 mg, 480 mumol) and potassium phosphate (221 mg, 960 mumol) in water: dioxane (10 mL) was degassed with argon for 10 minute. PdCl2(dppf)-DCM (39.1 mg, 48.0 mumol) was added to above reaction mixture and the solution was again purged with argon and refluxed for 16 hour at 100C. After completion of the reaction was observed by TLC ( Rf = 0.5 in 30% EtOH/Hexane), the reaction mixture was filtered through celite and concentrated. The residue was again dissolved in EtOAc (50 mL), washed with water, brine and evaporated. The crude residue was purified by combi flash chromatography (4 g Isco gold, hexane/EtOAc 70-30%) to give 2,6-bis(benzyloxy)-3-(1-methyl- 1H-pyrazol-3-yl)pyridine 24-2 (120 mg, 323 mumol, 67.4 %) as a white gummy solid. 1H NMR (400 MHz, DMSO-d6) delta 8.17 (d, J = 8.2 Hz, 1H), 7.65 (d, J = 1.9 Hz, 1H), 7.46-7.42 (m, 4H), 7.39-7.33 (m, 4H), 7.33-7.31 (m, 2H), 6.61 (d, J = 2.1 Hz, 1H), 6.51-6.49 (m, 1H), 5.46 (s, 2H), 5.37 (s, 2H), 3.85 (s, 3H). Synthesis

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); 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. 90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine, molecular formula is C6H4BrN3, 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. SDS of cas: 90993-26-3

Step 3: 7-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide To a stirred solution of 7-bromo-lH-imidazo[4,5-c]pyridine 5-oxide (425 mg, 1.99 mmol) and N,N- dimethylformaldehyde (5.5 mL) at 0 C was added N,N-diisopropylethylamine (1.05 mL, 5.96 mmol), tetrabutylammonium iodide (74 mg, 0.199 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (0.78 mL, 3.97 mmol) and the reaction mixture stirred for 30 min at RT. The reaction mixture was washed with water (10 mL) and extracted with dichloromethane (2 x 10 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) affording an approximate 3:2 mixture of 7-bromo-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide and 7-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 5-oxide N-(2- (trimethylsilyl)ethoxy)methane regioisomers as an orange foam (580 mg, 54%): H NMR (400 MHz, DMSO-d6; reported as an approximate 3:2 mixture of N-(2-(trimethylsilyl)ethoxy)methane isomers) delta 8.73 (d, = 1.5 Hz, 0.6 H), 8.60 (d, = 1.6 Hz, 1H), 8.38 (d, = 1.5 Hz, 1H), 8.36 (d, = 1.5 Hz, 0.6H), 8.10 (s, 1H), 8.09 (s, 0.6H), 5.76 (s, 1.3H), 5.48 (s, 2H), 3.63 – 3.59 (m, 1.4H), 3.56 – 3.50 (m, 2H), 0.97 – 0.91 (m, 3H), -0.01 (s, 9H), -0.02 (s, 6H). Step 4: 7-bromo-N-(tert-butyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyrid^ amine To a stirred solution of 7-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5- oxide (102 mg, 0.296 mmol) and 1 ,2-dichloroethane (1.5 niL) was added N,N-diisopropylethylamine (0.195 niL, 1.11 mmol), i-butylamine (0.039 mL, 0.37 mmol) and bromotripyrrolidinophosphonium hexafluorophosphate (180 mg, 0.385 mmol) and the reaction mixture stirred for 22 h at RT. The reaction mixture was washed with saturated sodium bicarbonate solution (10 mL) and extracted with dichlorome thane (2 x 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 50% ethyl acetate in heptane) affording an approximate 3:2 mixture of 7-bromo-N-(tert-butyl)-l-((2-(trimethy and 7-bromo-N-(tert-butyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-amine N- SEM regioisomers (47 mg, 40%): H NMR (400 MHz, DMSO-d6; reported as an approximate 3:2 mixture of N-SEM isomers) delta 8.00 (s, 0.7H), 7.95 (s, 1H), 7.81 (s, 0.7H), 7.77 (s, 1H), 6.02 (br s, 0.8H), 5.77 (s, 2H), 5.54 (s, 1.6H), 5.43 (br s, 1H), 3.63 – 3.57 (m, 3.7H), 1.02 – 0.89 (m, 3.8H), 0.00 (s, 6H), -0.02 (s, 9H). Step 5: N-(tert-butyl)-7-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purin-2- yl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridin-4-amine 4-cyclopropyl-6,6-dimethyl-2-(tributylstannyl)-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purine (64.5 mg, 0.12 mmol) and 7-bromo-N-(tert-butyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5- c]pyridin-4-amine (46 mg, 0.115 mmol) were dissolved in 1,4-dioxane (2.5 mL) in a microwave vial equipped with a stir bar and the mixture was purged with nitrogen gas for 10 min. Copper(I) thiophene-2-carboxylate (22 mg, 0.115 mmol) and tetrakis(triphenylphosphine)palladium(0) (13.3 mg, 0.012 mmol) were then added and the reaction mixture was microwaved at 140 C for 35 min. The reaction mixture was filtered through a celite bed and washed with dichlorome thane (10 mL). The filtrate was concentrated to dryness in vacuo, dissolved in ethyl acetate and washed with brine (10 niL). The organic layer was separated, dried over sodium sulfate and concentrated to afford crude N-(tert-butyl)-7-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purin-2-yl)-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridin-4-amine used for the next step without any further purification.

With the rapid development of chemical substances, we look forward to future research findings about 90993-26-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 866775-18-0, 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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.

Step 1: 3-Amino-6-cyclopropyl-5-(trifluoromethyl)picolinic acidA microwave vial was charged with amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (0.5 g, 1.754 mmol), cyclopropylboronic acid (0.753 g, 8.77 mmol), and 1,1’Bis(diphenylphosphosphino) ferrocene palladium dichloride (0.143 g, 0.175 mmol). The mixture was taken up as a solution in THF (6 ml) and flushed with N2, sealed and heated using microwave radiation at 150 C. for 20 minutes. The reaction mixture was filtered through Celite (filter material) and washed through with EtOAc (20 ml). The filtrate was partitioned between EtOAc (30 ml) and water (50 ml). The phases were separated and the organic portion was washed with brine (30 ml), dried over MgSO4, filtered and concentrated under vacuum.The crude material was taken up in EtOAc (20 ml) and dry loaded onto silica (2-3 g). Material then purified on the Combiflash Rf Teledyne ISCO System 100% Isohexane to 60% EtOAc:Isohexane to afford semi pure material which was used without further purification.

Statistics shows that 866775-18-0 is playing an increasingly important role. we look forward to future research findings about Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate.

Reference:
Patent; NOVARTIS AG; US2011/230483; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem