Tag: M.W:200-300

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 777899-57-7, name is Methyl 2-chloro-5-nitroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H5ClN2O4

The starting material of tert-butyl ethyl malonate (41.7 g, 222 mmol, 1.2 eq.) was dissolved in anhydrous DMF (100 mL), cooled to 0 C, and stirred for 0.5 h. NaH (14.8 g, 370 mmol, 2 eq.) was added. After stirring for 0.5 h, methyl 2-chloro-5-nitroisonicotinate (40.0 g, 185 mmol, 1.0 eq.) was slowly added and stirred at room temperature for 5 h. The reaction was completely monitored by TLC, quenched with water at 0 C, concentrated, and extracted with EA (3×500 mL). The filtrate was concentrated under reduced pressure and the crude product was purified by silica gel column chromatography (PE: EA = 10: 1) to give the purified product (35g, yield: 51.4%).

With the rapid development of chemical substances, we look forward to future research findings about 777899-57-7.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Yang Xiaoju; (118 pag.)CN109575016; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7169-97-3 ,Some common heterocyclic compound, 7169-97-3, molecular formula is C7H7BrN2O, 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.

N-(5-bromopyridin-2-yl)acetamide (4.30 g, 20 mmol), m-carboxyphenylboronic acid (3.66 g, 22 mmol) was added to a 250 ml pear-shaped bottle.Further, cesium carbonate (13.0 g, 40 mmol) and tetrakistriphenylphosphine palladium (1.2 g, 1 mmol) were successively added.To the above mixture was added 200 ml of acetonitrile/water (V: V = 3: 2). N2 protection,The oil bath was heated to 90 C for 48 h. After the reaction was completed, the reaction solution was cooled to room temperature and suction filtered.The filtrate was adjusted to pH 4 with 6 mol/L hydrochloric acid to precipitate a white solid.After suction filtration, the cake was vacuum dried to give the product 3.53 g, yield 69%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7169-97-3, its application will become more common.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (14 pag.)CN109824582; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67443-38-3, 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. 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine. A new synthetic method of this compound is introduced below.

a) 5 -bromo-2-(methyloxy)-3 -nitropyridine. To a stirred solution of 5-bromo-2-chloro-3-nitropyridine (86 mmol) in methanol (75 mL) at 0 0C was added drop wise a solution of 25% w/w sodium methoxide in methanol (20 mL, 87 mmol) and methanol (20 mL) over 10 min. After stirring at 0 0C for 1 h the reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was concentrated under vacuum to approximately half its volume then poured into ice water (-500 mL). The precipitate that formed was filtered, washed with cold water, and dried under vacuum to give the title product (98%) as a pale yellow solid. MS(ES)+ m/e 233.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67443-38-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39140; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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.

Step 209.2: To a solution of 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert- butyl ester (279mg) in MeCN (10ml) was added Cs2CO3 (407mg) followed by benzyl bromoacetate (0.2ml). The resulting white suspension was stirred at RT for 48h, diluted with EA and washed with water and brine. The aq. phases were extracted with EA. The combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 25g cartridge, DCM/MeOH 97/3 for 10CV) to afford 371 mg of oil. The oil was purified by preparative chiral HPLC (I) to afford the two regioisomers, both as mixture of benzyl and ethyl ester that formed during the evaporation of the fractions after HPLC purification: Step 209.3: The Boc protecting group of 1-benzyloxycarbonylmethyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester was cleaved using a method analogous to that of Example 16 step 16.4 to give (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester. Step 209.4: To a solution of (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (176mg) in MeOH was added formaldehyde (36.5% in water, 0.052ml_) followed by NaBH3CN (29mg) and AcOH (0.5ml_). The reaction mixture was stirred at RT overnight. DCM was added and the mixture was washed with sat. NaHCO3. The aq. layer was extracted with DCM, the combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 10g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in %B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV) to afford (5-methyl-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (39mg, yellow oil). (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester (1 1 1 mg, colourless oil). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 5H); 7.18 (s, 1 H); 5.21 (s, 2H); 4.89 (s, 2H); 3.50 (s, 2H); 2.86 (t, 2H, 6.0Hz); 2.76 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.89ppm and CH at 7.18ppm. (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1 -yl)-acetic acid benzyl ester (45mg, pale yellow solid). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 6H); 5.21 (s, 2H); 4.85 (s, 2H); 3.47 (s, 2H); 2.75 (t, 2H, 6.0Hz); 2.67 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.85ppm and CH2 at 2.67ppm. Step 215.2: The final compound was prepared using a method analogous to that of Example 14 step 14.2, (5-methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester replacing intermediate 14.1 and using MeOH instead of MeOH/AcOH. LC-MS (B): tR = 0.17min; [M+H]+: 196.29.

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; KELLER, Marcel; KIMMERLIN, Thierry; MEYER, Emmanuel; WO2013/114332; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-6-methoxypicolinic acid (5 g, 22 mmol) was dissolved in DMF (50 mL) and cooled to 0C under argon. DIPEA (7.66 mL, 44 mmol), ammonium chloride (1.77 g, 33 mmol) and HATU (12.6 g, 33 mmol) were added and the mixture was warmed to room temperature and stirred overnight. Water (50 mL) was added and the solid precipitate 5-bromo-6-methoxypicolinamide was collected by filtration(4.21 g, 83%). ?H NMR (DMSO, 400 MHz): 8.14 (d, 1H), 8.04 (br s, 1H), 7.71 (br s, 1H), 7.48 (d, 1H), 4.00 (s, 3H). LCMS (basic, 3.1 mm): RT 1.64 mi [MHj+ 232.9, purity 83%.

According to the analysis of related databases, 1214334-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1037223-35-0, 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.1037223-35-0, name is 2-Bromo-6-isopropylpyridine, molecular formula is C8H10BrN, molecular weight is 200.08, as common compound, the synthetic route is as follows.

Compd. 1B (5. 0g, 9. 50mmol), 2-bromo-6-Isopropylcyclohexanecarboxylic polypyridine (3. 0g, 19. 0mmol), sodium carbonate (7. 5g, 19. 0mmol) of dimethyl ether (100 ml)/ water solution (20 ml), tetrakis (triphenylphosphine) palladium (1. 0g, 0. 95mmol) in addition to 10 C, reflux in 12 hours. Ice water (100 ml) is added, the extracted with ethyl acetate (100 ml × 3 times) the reaction liquid. After cleaning the saturated solution, dried with sodium sulfate, filtration, concentrating, column chromatography (ethyl acetate/aminopentanenitrile = 10/1) by purification, yellow oilies compd. 2A is obtained. Yield 4. 0g yield at 83%.

Statistics shows that 1037223-35-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-6-isopropylpyridine.

Reference:
Patent; JAPAN POLYPROPYLENE CORP; JAPAN POLYETHYLENE CORP; KOBAYASHI, MINORU; UCHINO, HIDEFUMI; (40 pag.)JP2015/155397; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131803-48-0, Methyl 6-(bromomethyl)nicotinate, 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, 131803-48-0, blongs to pyridine-derivatives compound. COA of Formula: C8H8BrNO2

Example II (0492) 6-{[Bis(pyrazin-2-yl)amino]methyl}-N-hydroxypyridine-3-carboxamide (0493) (0494) II (0495) NaH (60%, 48.5mg, 1.21 mmol) was added to a solution of (3) (200mg, 1.15mmol) in DMF (7ml_) at 5C under N2(g). The reaction mixture was stirred for 20min then methyl 6-(bromomethyl)pyridine-3-carboxylate (345mg, 1.5mmol) was added as a solution in DMF (3ml_). The stirring was continued at 70C for 1 h. Reaction cooled to rt and poured onto water (100ml_). Brine (25ml_) was added and the aqueous was extracted with EtOAc (2 x 100ml_). Combined organics were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash column chromatography with CH2CI2/EtOAc (1 :0-0:1) then EtOAc/MeOH (1 :0-4: 1) to give (4) (129mg, 35%). (0496) 1 H NMR (500 MHz, Chloroform-d), deltaEta ppm: 9.04-9.13 (m, 1 H), 8.70 (s, 2H), 8.19 (s, 2H), 8.13 (dd, J=5.6, 2.3 Hz, 3H), 7.32 (d, J=8.2 Hz, 1 H), 5.55 (s, 2H), 3.86 (s, 3H). LCMS (ES): Found 322.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131803-48-0, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; WHALE, Andrew David; COLMAN, Lucy Mary; ROGERS, Helen Louise; (117 pag.)WO2017/208032; (2017); A1;,
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.911434-05-4, name is 5-Bromo-2-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.Recommanded Product: 911434-05-4

j00130j 5-Bromo-2-methyl-3-nitropyridine (2.00 g, 9.22 mmol) was dissolved in THF (92 mL) and the solution was cooled to -50 C under an atmosphere of argon. Vinylmagnesium bromide (1 M in THF, 27.6 mL, 27.6 mmol) was added in one portion and the reaction mixture turned orange. The reaction was allowed to stir at -40 C for 30 mm and then quenched the reaction with saturated ammonium chloride solution. The mixture was extracted with EtOAc, the combined organic layers dried with MgSO4 and concentrated by rotary evaporation. The crude material was purified by column chromatography to yield 4-bromo-7-methyl-1H-pyrrolo[2,3-c]pyridine (0.711 g, 36.6%). LCMS (FA): m/z = 211.0, 213.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,911434-05-4, 5-Bromo-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214353-79-3, 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 1214353-79-3, name is Methyl 5-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 5-bromo-6-chloropyridine-2-carboxylate (Ark Pharm, 360 mg, 1.4 mmol), copper(I) iodide (19 mg, 0.10 mmol) and dichloro[bis(triphenylphosphonio)]palladate (60 mg, 0.086 mmol) were placed in a vial. The vial was then evacuated and backfilled with nitrogen three times. After this 1,4-dioxane (6.2 mL) and triethylamine (300 L, 2.16 mmol) were added. The reaction was stirred for 5 min. Then (trimethylsilyl)acetylene (244 muIota_,, 1.72 mmol) was added and the resulting reaction mixture was stirred at 60 C for 3 h. After this time the reaction was quenched with water and product was extracted with EtOAc. The combined organic fractions were washed with brine, dried with a2S04 and solvent was evaporated under reduced pressure. The crude product was purified by chromatography on silica gel using Biotage Isolera apparatus to give the sub-title compound (370 mg, 97%). LCMS calc. for C12H15CINO2S1 (M+H)+ m/z = 268.1; found: 268.0.

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 1214353-79-3, Methyl 5-bromo-6-chloropicolinate.

Reference:
Patent; INCYTE CORPORATION; VECHORKIN, Oleg; LI, Yun-Long; ZHU, Wenyu; (232 pag.)WO2016/10897; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98027-80-6 , The common heterocyclic compound, 98027-80-6, name is 4-Bromo-2,6-dichloropyridine, molecular formula is C5H2BrCl2N, 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.

(2) In a 250 mL three-neck flask, flush with nitrogen.Added 0.02 mol of raw material 4-bromo-2,6-dichloropyridine,150ml DMF, 0.024mol 4-Biphenylboronic acid pinacol ester,0.0002mol palladium acetate, stirring, then add 0.03mol K3PO4 aqueous solution, heated to 130 C, refluxing reaction for 10 hours, sampling point plate,The reaction is complete. Natural cooling, add water,The mixture was filtered and dried in a vacuum ovenThe resulting residue was purified on a silica gel column to give compound intermediate A1;HPLC purity 99.5%, yield 88.3%.

The synthetic route of 98027-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Wang Fang; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (53 pag.)CN107602538; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem