Tag: M.W:200-300

Synthetic Route of 122851-69-8, 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. 122851-69-8, name is 3-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

A solution of cis-4-(2,3,6-trifluorophenyl)cyclohexanol (3.66 g) in THF (100 ml)was cooled to 0C, 60% sodium hydride (1.272 g) was added, and the mixture wasstirred under a calcium chloride tube dry atmosphere at room temperature for 10 min.To the reaction mixture was added 3-bromo-2-(chloromethyl)pyridine (4.92 g), and themixture was stirred at 70C for 3 hr. Water was added to the mixture at room temperature,and the mixture was extracted with ethyl acetate. The organic layer waswashed with saturated brine, dried over anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The residue was purified by silica gel chromatography(ethyl acetate/hexane) to give the title compound (3.73 g).MS, found: 401.0,403.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,122851-69-8, 3-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 920979-05-1, Adding some certain compound to certain chemical reactions, such as: 920979-05-1, name is 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid,molecular formula is C9H5F3N2O2, 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 920979-05-1.

10.3 5-(Trifluoromethyl)pyrrolo[3,2-b]pyridine-2-ethyl carboxylate; 1 mL (18.71 mmol) of concentrated sulfuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in Stage 10.2, in 10 mL of ethanol. It is stirred under reflux for 20 hours then the solution is cooled, and concentrated at reduced pressure. The resultant residue is then taken up in 50 mL of dichloromethane then washed successively with 20 mL of a saturated aqueous solution of sodium bicarbonate, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.19 g of product, which is used as it is in the next stage.

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. 920979-05-1, 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2010/41634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89364-04-5, 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.89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.9935, as common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, was added 0.05mol A-1,0.06mol raw material B-1, was added a mixed solvent (180ml THF to a three-necked flask of 500ml, 90ml H2O) was dissolved, nitrogen was stirred for 1 hour and then added 0.1mol K2CO3, 0.0005mol Pd (PPh3)4And heated to 80 , 20 hours, the reaction was observed by thin layer chromatography (TLC), until the reaction was complete.After cooling to room temperature, extracted with methylene chloride was added to the reaction system, liquid separation, the organic phase was spin evaporated under reduced pressure until no fraction.The resulting material was purified by silica gel column, to give the intermediate C-1.

The chemical industry reduces the impact on the environment during synthesis 89364-04-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Li Chong; Chen Haifeng; Zhang Zhaochao; Xu Haojie; (47 pag.)CN110372715; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 183483-29-6, name is 2-(2-Bromopyridin-4-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(2-Bromopyridin-4-yl)acetic acid

To a solution of 2-(2-bromo-4-pyridyl)acetic acid (300 mg, 1.39 mmol), diisopropylethylamine (538 mg, 4.17 mmol) and HATU (634 mg, 1.67 mmol) in DCM (15 mL) was added ethyl 2-amino-2-methyl-propanoate (256 mg, 1.53 mmol, HCl salt) and the reaction mixture was stirred at 20 C for 16 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 1:1) to give the title compound (430 mg, 94% yield) as a light yellow solid. LCMS: (ES+) m/z (M+H)+= 329.0, tR = 0.679.1H NMR (400MHz, CDCl3) delta = 8.33 (d, J = 5.2 Hz, 1H), 7.45 (d, J = 1.2 Hz, 1H), 7.22 (dd, J = 1.2, 5.2 Hz, 1H), 6.27 (br. s., 1H), 4.20 (q, J = 7.2 Hz, 2H), 3.49 (s, 2H), 1.57 (s, 6H), 1.26 (t, J = 7.2 Hz, 3H)

With the rapid development of chemical substances, we look forward to future research findings about 183483-29-6.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1018505-59-3 , The common heterocyclic compound, 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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.

The 4 – (2 – chloro -3 – fluoro – pyrazine amino) -2 – pyrimidine formic acid (1.35 g 1.2 eq), 5 – (4 – ethyl – piperazine -1 – yl) – piperidine -2 – amino (0.81 g 1 eq) and triethylamine (500 mul) in DMF (15 ml) in, then added HBTU (1.51 g 1.5 eq). The mixture stirring at room temperature to 16 hours, then EtOAc (50 ml) and saturated NaHCO3Solution (15 ml), and for separating each layer of EtOAc (2 × 15 ml) extraction the aqueous layer, the combined organic layer dried (MgSO4), filtering and evaporation to dryness, the residue through the column chromatography purification, and to obtain white solid compound of 1.42 g (yield: 62%).

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

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Zou Mingming; Hu Xiande; Sui Rongchun; Xu Man; (14 pag.)CN108689997; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-06-6, 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

According to the analysis of related databases, 886365-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206775-52-1 ,Some common heterocyclic compound, 1206775-52-1, molecular formula is C7H6BrNO2, 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) Tetrakistriphenylphosphine palladium (403 mg), phenylboronic acid (510 mg) and a 2 M sodium carbonate solution (3.5 mL) were sequentially added to a solution of 5-bromo-6-methoxypyridine-2-carbaldehyde (753 mg) in 1,2-dimethoxyethane (23 mL) in a nitrogen atmosphere, and the mixture was stirred at 80 C. for three hours. Water was added to the reaction solution at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1?1:1) and further purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6-methoxy-5-phenylpyridine-2-carbaldehyde (445 mg, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206775-52-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); 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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.name: 3-Bromo-2-chloro-6-picoline

In 21 mL of carbon tetrachloride, 3-bromo-2-chloro-6-methylpyridine (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90C for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol = 100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,185017-72-5, 3-Bromo-2-chloro-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SUGIMOTO, Tetsuya; TAKAHASHI, Hidekazu; MITSUYA, Morihiro; MASUKO, Norio; SOOTOME, Hiroshi; EP2821406; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 106047-28-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, 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, Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, blongs to pyridine-derivatives compound. Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

[00316] fer -Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2S03 (1.5 eq) was added via addition funnel. After completion of Na2S03 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1 -oxide (95%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem