Tag: M.W:100-200

Electric Literature of 824-52-2, 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 824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

b) 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde can be prepared as follows: Add 1.6 g of 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane to a suspension of 1 g of 5-methyl-1H-pyrrolo[2,3-b]pyridine in a mixture of 10 cm3 of water and 5 cm3 of acid acetic. Reflux the mixture under argon for four hours and thirty minutes, then add 30 cm3 of water to the hot mixture and leave to return to room temperature while stirring overnight. Then extract the mixture with three times 50 cm3 of ethyl acetate. Then combine the organic phases and wash with 3 times 50 cm3 of water, dry over magnesium sulphate and concentrate to dryness at reduced pressure to obtain 610 mg of a mixture containing 65% (by NMR) of 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde in the form of a yellow powder, for which the characteristics of the main product are as follows:

According to the analysis of related databases, 824-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; sanofi-aventis; US2009/253679; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1211536-01-4 ,Some common heterocyclic compound, 1211536-01-4, molecular formula is C6H5BrFN, 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 microwave vial was added 2-bromo-6-fluoro-3-methylpyridine (1355 mg, 7.13 mmol), tert-butyl piperazine-1-carboxylate (1338 mg, 7.18 mmol), anhydrous NMP (3.5 mL), and DIPEA (1.65 ml, 9.45 mmol). The resulting mixture was heated at 120 C for 16 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (100 mL), washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash chromatography (80 g Si02, 0-25% EtOAc in hexanes) to afford tert-butyl 4-(6-bromo-5-methylpyridin-2-yl)piperazine-1- carboxylate (46-1) as a waxy tan solid. HRMS m/z (M+H) 356.0971 measured, 356.0968 calculated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211536-01-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 851179-01-6, 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.851179-01-6, name is 3-Chloro-2,4-difluoropyridine, molecular formula is C5H2ClF2N, molecular weight is 149.5259, as common compound, the synthetic route is as follows.

A four-necked flask was charged with 2,4-difluoro-3-chloropyridine (29.9 g, 0.20 mol)Ethanol (240 mL),Hydrazine hydrate (80%, 25 g, 0.40 mol) was added dropwise with vigorous stirring,After heating and refluxing for 12 hours,The mixture was poured into 350mL water, analysisThe solid was filtered, washed with ethanol,Vacuum drying gave 18.7 g of 3-chloro-4-fluoro-2-hydrazinopyridine as yellowish solid in 58% yield.

Statistics shows that 851179-01-6 is playing an increasingly important role. we look forward to future research findings about 3-Chloro-2,4-difluoropyridine.

Reference:
Patent; Zhejiang Xin’an Chemical Group Co., Ltd.; Zhu Jianmin; Yu Shenluan; Li Qiaojun; Liu Chunjie; Fan Xiaotang; Jiang Zhe; Xu Yaqing; (19 pag.)CN104557860; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 167837-43-6 ,Some common heterocyclic compound, 167837-43-6, molecular formula is C8H8N2O2, 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.

Example 62; Preparation of (El-S-f-aminopyridin-S-v?-N-fCS-fluoro-S-methylbenzofblthiorjhen-?- ylimethvD-N-methylacrylamide hydrochloride;To a solution of (5-fluoro-l-methyl-lH-indol-2-yl)-N-methyhnethanamine (168 mg, 0.8 mmol) in DMF (5 mL) were added in sequential order (E)-3-(6-aminopyridin-3- yi)acrylic acid (120 mg, 0.73 mmol), 1-hydroxybenzotriazole (111 mg, 0.8 mmol), diisopropylethylamine (391 uL, 2.19 mmol), and N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide (160 mg, 0.8 mmol). The mixture was stirred at room temperature overnight, cooled in an ice bath and water added with rapid stirring. The product was extracted with ethyl acetate (3 x 1OmL), dried, filtered and concentrated. The crude free base was re-solvated in methylene chloride (1OmL) to which was added HCl (1 mL, 4M in dioxane), with the product precipitating out with the addition of ether. The title compound is triturated with ether (2 x 10 mL) to yield the product as a pale brown solid (76 mg, 25%): 1HNMR (300 MHz, DMSO-J6) delta 8.2-8.49 (m, 3H), 7.86-7.99 (m, IH), 7.46-7.64 (m, 2H), 7.16-7.29 (m, 2H), 6.99 (d, J= 12.0 Hz, IH), 4.83-5.13 (rotamers, 2s, 2H), 2.95-3.16 (rotamers, 2s, 3H), 2.41 (s, 3H); MS (ESI) m/e 356 (C19H18FN3OS + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,167837-43-6, its application will become more common.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
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

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 349-94-0, 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. 349-94-0, name is 5-Chloro-2-trifluoromethylpyridine. A new synthetic method of this compound is introduced below.

Step C 5-chloro-4-iodo-2-(trifluoromethyl)pyridine Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-chloro-2-(trifluoromethyl)pyridine (as prepared in the previous step, 5 g, 27.62 mmol, 1.00 equiv) in tetrahydrofuran (50 mL). LDA (3 g, 28.04 mmol, 1.05 equiv, as a THF solution) was added dropwise with stirring at -78 C. The resulting solution was stirred for 30 min at -78 C. A solution of I2 (7.4 g, 29.13 mmol, 1.05 equiv) in tetrahydrofuran (10 mL) was added dropwise with stirring at -78 C. The reaction mixture was stirred for an additional 2 h at -78 C., quenched with 15 mL of Na2S2O3(1M) and diluted with 100 mL of water. The resulting mixture was extracted with 3*50 mL of ether. The combined organic layers were washed with 50 ml brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (0:1), yielding 5-chloro-4-iodo-2-(trifluoromethyl)pyridine as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,349-94-0, 5-Chloro-2-trifluoromethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhang, Xuqing; Sui, Zhihua; Lanter, James C.; US2011/306592; (2011); 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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2ClFN2O2

To a solution of Compound 4 (3 g, 12.22 mmol, 1 eq) and 2-chloro-3-fluoro-5-nitropyridine (2.37 g, 13.44 mmol, 1.1 eq) in DMF (20 mL) was added K2CO3 (3.38 g, 24.44 mmol, 2.0 eq) in one portion at 16 C, followed by heating with stirring at 70 C for 2 h. The reaction mixture was poured into water, and the resulting solids were filtered. The filter cake washed with water (20 mL) and dried under vacuum to give the Compound 7 as a yellow solid (3.5 g, 68.1% yield). NMR (400 MHz, DMSO-d6) delta 9.43 (d, 1H), 9.17 (dd, 1H), 8.53 (s, 1H), 8.10 (d, 1H), 6.67 (s, 1H), 6.29 (d, 1H), 3.83 (s, 3H), 3.74 (s, 3H); MS (El) for C17H12FN3O6, found 374.0 (MH+).

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, 1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem