Tag: M.W:100-200

Synthetic Route of 896139-85-8, 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 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of imidazo[l,2-a]pyridin-7-ol (CAS 896139-85-8; 35 mg, 0.26 mmol) in dry DMF (3 mL) is added NaH (60% in mineral oil, 42 mg, 1.04 mmol) and the mixture is stirred at RT for 10 min. Methyl l-bromocyclopentane-l-carboxylate (CAS 51572-54-4; 143 pL, 1.04 mmol) is added and the mixture is heated at 50 C for 20 h. The reaction mixture is concentrated and the residue is diluted with water and DCM. The aqueous phase is extracted with DCM. Organic layers are combined, dried over Na2S04, filtered and concentrated to afford the expected compound. LCMS: MW (calcd): 260.3; m/z MW (obsd): 261.6 (M+H)

According to the analysis of related databases, 896139-85-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; DESROY, Nicolas; JONCOUR, Agnes, Marie; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; BUCHER, Denis; AMANTINI, David; DE VOS, Steve, Irma, Joel; BRYS, Reginald, Christophe, Xavier; (396 pag.)WO2019/238424; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 129012-04-0, Adding some certain compound to certain chemical reactions, such as: 129012-04-0, name is 6-Bromopyridine-2,3-diamine,molecular formula is C5H6BrN3, 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 129012-04-0.

Preparation Example 9-3 5-Bromo-2-methyl-1H-imidazo[4,5-b]pyridine 2,3-Diamino-6-bromopyridine (8.16 g) and triethyl orthoacetate (12.0 ml) were mixed in acetic acid (41 ml), and the mixture was refluxed under heating for 29 hr.. The mixture was allowed to cool and the solvent was evaporated to give a crude product (10 g).. This was dissolved in a sufficient amount of dichloromethane.. Anhydrous potassium carbonate and active carbon were added and the mixture was stirred at room temperature.. The insoluble matter was filtered off and the solvent was evaporated to give the objective compound (7.59 g) as a pale-yellow powder. 1H-NMR(DMSO-d6): 2.51(3H, s), 7.31(1H, d, J=8 Hz), 7.82(1H, d, J=8 Hz) Mass(ESI): m/e 212, 214 (M+H)+

According to the analysis of related databases, 129012-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6348474; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 490-11-9, name is Pyridine-3,4-dicarboxylicacid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a mixture of pyridine-3,4-dicarboxylic acid (10.00 g, 60.00 mmol, 1 eq) and a catalytic amount of DMAP (50 mg) in 300 mL of anhydrous MeOH was added dropwise SOCl2 (21.4 mL, 300.00 mmol, 5 eq) at 0C. The reaction mixture was heated to reflux for 48 h, cooled to room temperature and concentrated in vacuo. The crude product was dissolved in CH2C12 (200 mL), and the solution was washed with saturated K2C03 aqueous solution and water (50 mL), dried over anhydrous Na2S04 and concentrated in vacuo to afford the title compound as pale yellow oil (8.00 g, 68.00 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 196.05 (M+1).

The synthetic route of 490-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

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 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

Related Products of 22282-99-1, 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.22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

To a stirred solution of 4-bromo-2- methylpyridine (3 g, 17.44 mmol) and diethyl carbonate (2.75 ml, 22.67 mmol) in THF (30 ml)was added LDA (4mL) (2M in THF/hept/ethylbenzene) at -78C. The solution was stirred for 1 h prior to the addition of another portion of LDA (4.00 mL). Stirring was continued at -70C for one more hour and then the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (Na2504). The solvent was evaporated and the residue was purified byflash columnchromatography on silica gel (0-100% EtOAc in Hex) to give the title compound. LC/MS =245.75 [M+lj

The chemical industry reduces the impact on the environment during synthesis 22282-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem