Tag: M.W:100-200

Related Products of 24100-18-3, 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. 24100-18-3, name is 2-Bromo-3-methoxypyridine. A new synthetic method of this compound is introduced below.

Step A 2-Bromo-3-methoxy-6-nitropyridine To a 500 mL round bottomed flask fitted with a Teflon stir bar and a thermometer was added 90 mL of concentrated sulphuric acid and 37.6 g of 2-bromo-3-methoxypyridine (200 mmol). The flask was warmed in an oil bath to 60 C. Added slowly over 1h 16.5 mL (350 mmol) of fuming nitric acid (90%, d=1.50). Maintain the temperature between 60 and 70 during the addition. Stir at 60 for 3h after the addition was complete, then at room temperature overnight. By TLC (70/30 hex/EtOAc) is consumed. The product mixture was poured into 600 mL of ice/water, from which the product precipitated. This material was filtered, washed with 3*200 mL of cold water and then 100 mL of saturated sodium bicarbonate. After drying in the filter funnel in a stream of air, the remaining water was removed under reduced pressure, to give 16.5 g of a solid. H NMR (400 MHz, CDCl3): delta 8.27(d, J=8 Hz,1H); 6.32(d, J=8 Hz,1H); 4.06(s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24100-18-3, 2-Bromo-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5929094; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6937-03-7, 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. 6937-03-7, name is Methyl 2-aminoisonicotinate. A new synthetic method of this compound is introduced below.

(2-Amino-pyridin-4-yl)-methanol (2-4) 2-Amino-isonicotinic acid methyl ester (6.0 g, 39.4 mmol) was dissolved in 80 mL anhydrous THF in a flame dried round bottom flask under nitrogen gas. The solution was cooled to -45° C. and LAH (39.4 mL, 1M in THF) was added slowly. The reaction was allowed to warm to 0° C. and was quenched by the addition of 15 mL of 1M NaOH (aq). The solution was filtered and the solid was washed with THF. The filtrate was concentrated to afford the pure product. 1H NMR (DMSO-d6) delta7.79 (d, 1H, J=5.2 Hz), 6.41 (s, 1H), 6.38 (d, 1H, J=5.9 Hz), 5.79 (bs, 2H), 5.19 (t, 2H, J=5.7), 4.35 (d, 2H, J=5.6 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6937-03-7, Methyl 2-aminoisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Ren, Yu; Karki, Shyam B.; Zhao, Matthew M.; Bidodeau, Mark T.; US2004/23981; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 871836-51-0, 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.871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-IH-pyrazolo[4,3-clpyridine (100 mg, 0.6Smmoi) (3 mL) was added NaI-l (78 mg, 1.95 mmol, 60 wt% in oil) at 0C under N2. The mixture was stirred at 0C for 40 minutes. Mel (277 mg, 1,95 mmol) was added at 25C. The mixture wasstirred for another 2 hours. The mixture was quenched with saturated Ni-14C1 aqueous solution and extracted with ELOAc (20 mL x 3). The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to give the title compound 56 (50.2 mg) as yellow oil, 57 (30 mg) as yellow oil. LRMS miz (M+H) 168.1, 170.1 found, 168.0, 170.1 required.

The chemical industry reduces the impact on the environment during synthesis 871836-51-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 769-28-8, Adding some certain compound to certain chemical reactions, such as: 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C8H8N2O, 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 769-28-8.

A 100 mL Teflon-sealed flask was charged with the 2-pyridone 1m(296 mg, 2.0 mmol), diaryliodonium salts 2r (1.695 g, 3.0 mmol, 1.5equiv), and Cs2CO3 (975 mg, 3.0 mmol, 1.5 equiv) under air atmosphere.DCE (20 mL) was then added to the flask. The reaction mixturewas stirred at 120 C until the 2-pyridone 1m was consumedcompletely (monitored by TLC). At this time, the solvent was removedin vacuo and the residue was purified by flash column chromatography(the crude residue was dry loaded on silica gel, 1:10 EtOAc/PE) toprovide the desired product 5; yield: 485 mg (83%); white solid; mp102-103 C.IR (film): 3073, 2922, 2229, 1600, 1449, 1327, 1179, 799 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.54-7.48 (m, 3 H), 7.39 (d, J = 7.2 Hz,1 H), 6.86 (s, 1 H), 2.54 (s, 3 H), 2.37 (s, 3 H). 13C NMR (100 MHz, CDCl3): delta = 126.8, 161.1, 155.1, 152.9, 132.3 (q, J =32.1 Hz), 129.9, 124.9, 122.2 (q, J = 269.1 Hz), 121.9 (q, J = 3.6 Hz),119.7, 118.8 (q, J = 3.6 Hz), 114.3, 95.3, 24.4, 20.2.HRMS (ESI): m/z (M + H)+ calcd for C15H12F3N2O: 293.0902; found:293.0891.

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. 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xiao-Hua; Ye, Ai-Hui; Liang, Cui; Mo, Dong-Liang; Synthesis; vol. 50; 8; (2018); p. 1699 – 1710;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17228-69-2 ,Some common heterocyclic compound, 17228-69-2, molecular formula is C6H6ClNO, 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 suspension of 2-chloro-4-methoxypyridine (250 mg; commercial), 2-benzyloxy- 5-formylphenylboronic acid (455 mg; commercial), K2C03 (1.65 g) in water (3 mL) and DMF (12 mL) was degassed with nitrogen, treated with bis(triphenylphosphine)palladium(II) di chloride (48 mg) and heated for 3 h at 100C. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between water and EA. The aq. layer was extracted with EA. The combined org. layers were washed with water and brine, dried over MgS04; evaporated under reduced pressure and purified by CC (Hept to Hept/EA 2:3) to yield a light yellow solid (309 mg; 60% yield). MSI (ESI, m/z): 320.1 [M+H+]; tR = 0.66 min.

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. 17228-69-2, 2-Chloro-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; HUBSCHWERLEN, Christian; RUEEDI, Georg; ZUMBRUNN, Cornelia; WO2014/170821; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58481-11-1, 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 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-chloroisonicotinate (0.996 g, 5.80 mmol), potassium carbonate (1.042 g, 7.54 mmol), 4,4,5,5-tetramethyl-2-(3-methyl-4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1.66 g, 5.80 mmol) and PdCl2 (dppf) (0.105 g, 0.15 mmol) were mixed in methanol (20 mL) in two microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. The solution was partitioned between water and ethyl acetate. The organic layer was isolated, dried over Na2SO4, filtered through celite and the solvent was evaporated. Automated column chromatography using the Biotage equipment. Gradient eluation using heptane-ethyl acetate, 0percent to 50percent. Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-isonicotinate (1.22 g, 71percent) was isolated. 1H NMR (600 MHz, cdcl3) delta 2.57 (s, 3H), 3.99 (s, 3H), 7.70 (d, 1H), 7.81 (dd, 1H), 7.91 (d, 1H), 7.98 (s, 1H), 8.29 (s, 1H), 8.84 (d, 1H).

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-64-4, 2-Chloro-5-methylpyridine, 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, Formula: C6H6ClN, blongs to pyridine-derivatives compound. Formula: C6H6ClN

Triphenylphosphine (430 mg, 1 .64 mmol) was added to a solution of 2-chloro-5- fluorophenol (200 mg, 1 .37 mmol) in tetrahydrofuran (2 mL). The reaction mixture was cooled to 0 °C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (213 mg, 1 .64 mmol) was added, followed by DIAD (0.32 mL, 1 .6 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 10percent-50percent EtOAc-heptane gradient to give the title compound (264 mg, 64percent) as a yellow oil. 1H NMR (400 MHz, CDCI3) delta 2.50-2.61 (m, 2 H), 2.78 (ddd, J = 14, 7, 4 Hz, 2 H), 3.18-3.28 (m, 1 H), 3.76 (s, 3 H), 4.91 (quin, J = 7 Hz, 1 H), 6.49 (dd, J = 10, 3 Hz, 1 H), 6.63 (td, J = 8, 3 Hz, 1 H), 7.30 (dd, J = 9, 6 Hz, 1 H); LC-MS (LC-ES) M+H = 259, 261 (CI pattern).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 144100-07-2, 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 144100-07-2, name is 2-Bromo-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydrogen (909.07 mg, 22.73 mmol, 60% purity) was dissolved in anhydrous THF (5 mL), the reaction was placed in an ice bath, replaced with nitrogen for 3 times, 2-bromo-6-fluoropyridine (2 g, 11.36 mmol), and 1-methylimidazolidinone (2.28 g, 22.73 mmol) were added at 0C, the mixture was stirred at 70C for 16 hours. Water (20 mL) was added to quench the reaction, then extracted with EA (3×20 mL), the organic phase was washed by saturated brine (20 mL), dried over anhydrous sodium sulfate, the filtrate was concentrated to give the crude product, the crude product was purified by column to give the 56-1. 1H NMR (400MHz, CDCl3) delta = 8.23 (d, J=8.5 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.05 (d, J=7.5 Hz, 1H), 4.10 – 3.93 (m, 2H), 3.53 – 3.40 (m, 2H), 2.95 – 2.85 (m, 3H), MS m/z:256.10 [M+H]+

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 144100-07-2, 2-Bromo-6-fluoropyridine.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 24484-93-3, Adding some certain compound to certain chemical reactions, such as: 24484-93-3, name is Methyl 4-chloropicolinate,molecular formula is C7H6ClNO2, 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 24484-93-3.

Preparation of 4-chloro-N-(methyl-d3)picolinamide A2 To a three-necked bottom flask with tetrahydrofuran (250 mL), methyl 4-chloro-2-picolinate (50 g, 291 mmol, 1 eq) was added. N-(methyl-d3)amine hydrochloride (31 g, 437 mmol, 1.5 eq) and anhydrous potassium carbonate(400-mesh, 80 g, 583 mmol, 2 eq) were added with stirring. After the mixture was stirred at room temperature for 20 h, water (250 mL) and methyl tert-butyl ether (150 mL) were added. The mixture was stirred and separated. The aqueous layer was extracted with methyl tert-butyl ether (100 mL). The organic phases were combined, dried over anhydrous sodium sulfate and filtered. The solvent in the filtrate was removed under reduced pressure to obtain the product (48 g, purity 99%, yield 96%) as light yellow liquid. 1H NMR(DMSO-d6, 400 MHz): delta7.64(dd, J = 2Hz, 5.2Hz, 1H), 7.97(d, J = 1.6Hz, 1H), 8.54(d, J = 5.2Hz, 1H), 8.74(br, 1H). MS (ESI, m/z) calcd. for C7H4D3ClN2O: 173, found : 174 [M +H]+

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. 24484-93-3, Methyl 4-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Zelgen Biopharmaceutical Co., Ltd.; FENG, Weidong; GAO, Xiaoyong; DAI, Xiaojun; EP2548867; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 68325-15-5 ,Some common heterocyclic compound, 68325-15-5, molecular formula is C6H3ClN2, 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 (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (20 mg, 0.061 mmol) in THF (0.615 mL) was added 1M potassium teri-butoxide in THF (73.75 mu?, 73.75 muiotaetaomicron?) was added 3-chloroisonicotinonitrile (10.22 mg, 73.75 muiotaetaomicron?) at room temperature . The reaction mixture was stirred for 16 h and then concentrated. The residue was purified by TLC (silica gel, 50% EtOAc/hexanes) to give the title compound (14.1 mg, 0.033 mmol, 53.7% yield). Exact mass calculated for C24H33N3O4: 427.3, found LCMS m/z = 428.4 [M+H]+; ‘ll NMR (CDCI3 , 400 MHz) delta ppm 1.44-1.75 (m, 8H), 1.47 (s, 9H), 1.87-2.03 (m, 6H), 2.09-2.16 (m, 2H), 3.51-3.58 (m, IH), 3.78-3.87 (m, IH), 4.15-4.33 (m, 2H), 4.57-4.63 (m, IH), 7.45 (d, = 5.0 Hz, IH), 8.32 (d, = 5.0 Hz, IH), 8.47 (s, IH).

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. 68325-15-5, 3-Chloro-4-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem