Category: pyridine-derivatives

Reference of 122306-01-8 ,Some common heterocyclic compound, 122306-01-8, molecular formula is C6H6BrNO, 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.

This compound was synthesised as previously reported and analysis matched with literature values.[30] microscopy of the adjacent tissue immunohistochemically stained with 1E8 antibody. Scale bars indicate 100 mm. (6-Bromopyridin-3-yl)methanol (2) (2.93 g, 11.3mmol) was dissolved in dichloromethane (40mL) and treated with an excess of thionyl chloride (7mL). The reaction was monitored by TLC (33% ethyl acetate in petroleum spirits; Rf 0.81) and once complete, volatiles were removed by evaporation. The residue was then suspended in saturated NaHCO3 (50mL) and extracted with ethyl acetate (2_50mL). The organic extracts were combined, dried over MgSO4, and evaporated to dryness to yield a brown oil, which yielded a crystalline white solid upon standing. The solid was suspended in pentane and isolated by filtration, washed with pentane, and air-dried to give a crystalline colourless solid (2.13 g, 10.3mmol, 91% yield). dH (400MHz, CDCl3) 8.37 (d, 4JHH 1.9, 1H, ArH), 7.60 (dd, 3JHH 8.2, 4JHH 2.4, 1H, ArH), 7.50 (d, 3JHH 8.2, 1H, ArH), 4.54 (s, 2H, CH2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122306-01-8, its application will become more common.

Reference:
Article; McInnes, Lachlan E.; Noor, Asif; Roselt, Peter D.; McLean, Catriona A.; White, Jonathan M.; Donnelly, Paul S.; Australian Journal of Chemistry; vol. 72; 10; (2019); p. 827 – 834;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1254473-66-9, Adding some certain compound to certain chemical reactions, such as: 1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol,molecular formula is C7H7Cl2NO, 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 1254473-66-9.

MsCl (32g, 0.28mol) was added in batches to a solution of a mixture of Example 1E (36g, 0.91mol) and triethylamine (21g, 0.21mol) in dichloromethane (1 L) at 0C. The reaction was stirred at 0C for 3 hours and thenquenched with water (100mL) in an ice bath and stirred for 1 hour. After layering, the organic phase was washed withsaturated sodium bicarbonate solution (200mL 3 3) and brine (200mL), then dried over anhydrous sodium sulfate,filtered and the filtrate was concentrated to give a residue that was purified by flash silica gel column chromatographyto give the title compound (pale yellow, 50g, yield 98%).

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. 1254473-66-9, 1-(3,5-Dichloropyridin-4-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Harbin Zhenbao Pharmaceutical Co., Ltd.; Medshine Discovery Inc.; CHEN, Shuhui; CHEN, Zhengxia; DAI, Meibi; XIE, Cheng; LI, Peng; ZHANG, Yang; LIANG, Guibai; WANG, Qiang; LIAO, Jiangpeng; SUN, Fei; HU, Guoping; LI, Jian; (166 pag.)EP3333157; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 136888-17-0 , The common heterocyclic compound, 136888-17-0, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridin-2(3H)-one, molecular formula is C7H5ClN2O, 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 a degassed mixture of l,4-dioxane (20 mL) and water (3.0 mL) were added 5- chloro- 177-pyrrolo[2,3-c]pyridin-2(377)-onc (step 1 intermediate) (300 mg, 1.78 mmol) and (2-fluoro-6-methoxyphenyl)boronic acid (453 mg, 2.67 mmol) and the mixture was evacuated for 15 min. XPhos Pd G2 (140 mg, 0.18 mmol) and tribasic potassium phosphate (756 mg, 3.56 mmol) were added to the mixture. The resulting reaction mixture was heated on a pre-heated oil bath at 90 C for 2 h. The mixture was cooled to RT and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to yield 140 mg of the desired compound. 1 H NMR (400 MHz, DMSO-de) d 3.61 (s, 2H), 3.78 (s, 3H), 6.88 (t, J= 9.2 Hz, 1H), 6.96 (d, J = 8.4 Hz, 1H), 7.27 (s, 1H), 7.36-7.44 (m, 1H), 8.15 (s, 1H), 10.62 (s, 1H).

The synthetic route of 136888-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICHNOS SCIENCES S.A.; CHAUDHARI, Sachin, Sundarlal; GHARAT, Laxmikant, Atmaram; IYER, Pravin; DHONE, Sachin, Vasantrao; ADIK, Bharat, Gangadhar; WADEKAR, Prashant, Dilip; GOWDA, Nagaraj; BAJPAI, Malini; (233 pag.)WO2020/70331; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, 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, HPLC of Formula: C11H18N4, blongs to pyridine-derivatives compound. HPLC of Formula: C11H18N4

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

The synthetic route of 1018505-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 582303-10-4, 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. 582303-10-4, name is (2,6-Dimethylpyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a mixture of methyl ( 4-chloro-6-hydroxy-l- benzothiophen-3-yl) acetate (110 mg) and THF (dry) (5 mL) were added (2 , 6-dimethylpyridin-3-yl) methanol (58.8 mg) , tri-n- butylphosphine (0.159 mL) and ADDP (130 mg) at room temperature. The mixture was stirred at room temperature for 12 h. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (139 mg) . XH NMR (300 MHz, CDC13) delta 2.54 (3H, s) , 2.57 (3H, s) , 3.73 (3H, s), 4.11 (2H, s), 5.05 (2H, s) , 7.02 (1H, d, J = 7.9 Hz), 7.06- 7.09 (1H, m) , 7.13 (1H, s) , 7.29 (1H, s) , 7.58 (1H, d, J = 7.9 Hz) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1247503-48-5 , The common heterocyclic compound, 1247503-48-5, name is 6-(2,2,2-Trifluoroethoxy)picolinic acid, molecular formula is C8H6F3NO3, 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 a solution of 6-(2,2,2-trifluoroethoxy)picolinic acid (2.2 g, 10 mmol, 1.0 equiv) in methanol (20 mL) were added 2 drops of H2SO4 (con.). The mixture was stirred at 20C for 20 hours, diluted with H2O (100 mL) and extracted with DCM (3*20 mL). The combined organic phase was dried over anhydrous sodium sulfite and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EA = 20/1) to afford the title compound methyl 6-(2,2,2-trifluoroethoxy)picolinate as a colorless oil (2.1 g, 88% yield). LC-MS: m/z 236.1 (M+H)+

The synthetic route of 1247503-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANNAPURNA BIO, INC.; TANG, Haifeng; HANSON, Michael; BOYCE, Sarah; NIE, Zhe; (461 pag.)WO2020/73011; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65550-78-9 ,Some common heterocyclic compound, 65550-78-9, molecular formula is C6H5BrIN, 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.

A. 5-Iodo-3-methyl-2-methoxy-pyridine. To a solution containing 2-bromo-5-iodo-3-methyl-pyridine (4.80 g, 16.0 mmol) in DMSO (15 ML) is added methanolic NaOMe (3.33 M, 5.3 ML, 17.7 mmol) at 0 C. The solution is allowed to warm to ambient temperature and then heated at 70 C. for 1 hour.The reaction mixture is diluted with diethyl ether (300 ML) and water (200 ML) and the layers are separated.The organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated.The crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1) to provide 2.86 g (71%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) delta2.12 (s, 3H), 3.90 (s, 3H), 7.60 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H) ppm; MS (EI): m/z 249 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65550-78-9, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; US2004/102450; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1206775-52-1, 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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde. A new synthetic method of this compound is introduced below.

Preparation 79(5-B romo-6-methoxypyrid i n-2-yl)-N-methyl methanam ine5-Bromo-6-methoxypicolinaldehyde of preparation 78 (69 mg, 0.32 mmol) in a solution of NH2CH3 in THF (2M, 3ml_) was stirred under nitrogen at room temperature for 45 mins, and LCMS showed a mass of 230 which indicated the presence of the iminium ion. Sodium borohydride (36.2 mg, 0.957 mmol) was added, and the reaction was stirred at room temperature overnight. The desired product was detected by LCMS, and the reaction was quenched with MeOH (0.5 mL) and water (10ml), then partitioned with EtOAc (10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound as a yellow oil (47 mg), which was taken into the next step without further purification.MS: ESI+ m/z 231 [MH]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206775-52-1, 5-Bromo-6-methoxypicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 90993-26-3, Adding some certain compound to certain chemical reactions, such as: 90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine,molecular formula is C6H4BrN3, 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 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).

According to the analysis of related databases, 90993-26-3, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 60289-67-0, 1-(Pyridin-3-yl)propan-1-amine, 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, 60289-67-0, blongs to pyridine-derivatives compound. HPLC of Formula: C8H12N2

To a stirred solution of 1-(pyridin-3-yl)propan-1-amine (355.8 mg, 2.61 mmol, 2.00 equiv.) and 4-chloro-5-(4-oxopiperidin-1-yl)-2,3,4,5-tetrahydropyridazin-3-one (300 mg, 1.31 mmol, 1 equiv.) in DMF(10 mL) were added 1-azido-4-nitrobenzene (300.1 mg, 1.83 mmol, 1.40 equiv.) and Zn(OAc)2(239.7 mg, 1.31 mmol, 1 equiv.) at room temperature. The solution was stirred at 60 degrees Celsius for 16 h. The resulting mixture was concentrated under reduced pressure. The crude product (200 mg) was purified by Prep-HPLC with the following conditions (Column: XBridge Prep C18 OBD Column 19×150mm 5um; Mobile Phase A: Water(10 mmol/L (1117) NH4HCO3), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 23% B to 55% B in 7 min; 254/220 nm; Rt: 6.4 min) to afford 4-chloro-5-[1-[1-(pyridin-3-yl)propyl]-1H,4H,5H,6H,7H- [1,2,3]triazolo[4,5-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one (150mg,30.88%) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60289-67-0, its application will become more common.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem