Tag: M.W:200-300

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. 39919-65-8, name is 2,5-Dibromo-6-methylpyridine, molecular formula is C6H5Br2N, 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. name: 2,5-Dibromo-6-methylpyridine

Add to the reaction flask3,6-dibromo-2-methylpyridine (1.0 g, 3.9 mmol)And anhydrous ether (10 mL) were cooled to -78C,N-BuLi (1.6 M in hexanes, 2.4 mL, 3.9 mmol) was added dropwise,After stirring for 1 hour, anhydrous DMF (307 mg, 4.2 mmol) was added,The reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride solution (10 mL) was added,Ethyl acetate (20 mL x 3). Combine organic phase,Saturated sodium chloride solution (20mL), dried over anhydrous sodium sulfate, suction filtration,Concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / petroleum ether = 1: 10)The resulting residue was purified to give the title compound (0.4 g, white solid) in 51% yield.

With the rapid development of chemical substances, we look forward to future research findings about 39919-65-8.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

b) 4-(Benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride A suspension of 4-(benzyloxy)pyridin-2(1H)-one (71 mg, 0.35 mmol), tert-butyl 8-bromo-6-tosyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate (202 mg, 0.389 mmol), CuI (81 mg, 0.43 mmol), 8-hydroxyquinoline (62 mg, 0.43 mmol) and Cs2CO3 (127 mg, 0.389 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. The suspension was put under N2 and stirred at 135 C. for 4.5 h. The suspension was cooled, 9:0.9:0.1 CH2Cl2/MeOH/NH4OH (10 mL) was added, and the resulting suspension was stirred at 25 C. for 30 min. The suspension was passed through a plug of silica gel, and the filtrate was washed with brine. The resulting solution was dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded 190 mg of a yellow solid. NaOH (594 mg, 14.8 mmol) was added to a solution of the yellow solid in 1:1 MeOH/CH2Cl2 (20 mL) under N2, and the resulting suspension was stirred at reflux for 16 h. The reaction was cooled, H2O was added, and the resulting suspension was filtered. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded a green solid. Preparative HPLC (Phenomenex Luna C18 (2), 250.0*50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) afforded 50 mg of a white powder. 2 N HCl in Et2O (200 mL) was added to a solution of the white powder in 1:1 CH2Cl2/MeOH (4 mL) under N2, and the resulting suspension was stirred at 25 C. for 18 h. The suspension was filtered, and the solid was washed with Et2O to afford the title compound (35 mg, 23%) as a white solid: mp 258-260 C.; 1H NMR (500 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.06 (br s, 2H), 7.57-7.35 (m, 7H), 7.25 (s, 1H), 6.90 (d, J=8.0 Hz), 6.11-6.07 (m, 1H), 5.96 (s, 1H), 5.15 (s, 2H), 3.45-3.30 (m, 4H), 3.20-3.15 (m, 2H), 3.12-3.06 (m, 2H); ESI MS m/z 386 [M+H]+.

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Intermediate 1; 4-Iodo-1H-pyridin-2-one; To 10.0 g (41.8 mmol) 2-chloro-4-iodopyridine in 100 mL AcOH are added 17.1 g (208 mmol) NaOAc and the reaction mixture is heated at 180 C. for 2 h in a microwave oven. DCM and water are added to the reaction mixture and the layers are separated. The organic layer is washed with water, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is triturated with TBME.C5H4INO (M=221.0 g/mol),ESI-MS: 222 [M+H]+ Rf (TLC): 0.3 (silica gel DCM/MeOH 9/1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 78607-36-0 ,Some common heterocyclic compound, 78607-36-0, molecular formula is C5H3ClIN, 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 31K 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione To a solution of 0.8 g of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride obtained in stage c) of Example 7 in 50 mL of dioxane are successively added under argon 0.628 g of 2-chloro-3-iodopyridine, 2.8 g of caesium carbonate, 150 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (xantphos) and 49 mg of palladium diacetate. The reaction mixture is heated at 90 C. for 3 hours and then filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluding with a mixture of cyclohexane and ethyl acetate (70/30 by volume) to give 0.51 g of 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows: 1H NMR spectrum at 400 MHz: 1.31 (s, 9H); 1.43 (s, 6H); 4.57 (s, 2H); 6.89 (dd, J=1.5 and 5.5 Hz, 1H); 7.11 (broad s, 1H); 7.39 (m, 3H); 7.52 (d, J=8.5 Hz, 2H); 8.00 (dd, J=2.0 and 5.0 Hz, 1H); 8.10 (d, J=5.5 Hz, 1H); 8.55 (m, 2H). Mass Spectrum (ES): m/z=478 [M+H]+; m/z=476 [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. 78607-36-0, 2-Chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2009/82379; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1289093-31-7, 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 1289093-31-7 as follows.

Preparation 14: methyl 1 -i5-chloro-6-isobutoxypyridin-3-yl)-3-cvclopropyl-1 H- indazole-5-carboxylate; A mixture of methyl 3-cyclopropyl-1 H-indazole-5-carboxylate [preparation 9] (100mg, 0.396mmol), Cul (7.6mg, 0.40mmol), K3P04 (168mg, 0.792mmol), and 5-bromo-3- chloro-2-isobutoxy-pyridine [preparation 30] (105mg, 0.396mmol) was added to a septum sealed reaction vial and degassed. A solution of trans-N, N’- dimethylcyclohexane-1 ,2-diamine in toluene (2ml) was added. The mixture was degassed and filled with nitrogen three times, then stirred at 1 10C for 4 days. The mixture was allowed to cool and then partitioned between water (5ml) and DCM (5ml). The DCM phase was separated and the aqueous extracted with further DCM (5ml). The extracts were combined and evaporated onto silica. Purification by column chromatography (ISCO Companion, silica 12g, eluted with a gradient of heptane to 40% EtOAc in heptane) gave the title compound as clear oil (100.4mg).1 H NMR (400 MHz, CDCI3) delta ppm 1 .07 (d, 6H), 1 .19-1 .12 (m, 4H), 2.18 (septuplet, 1 H), 2.27-2.34 (m, 1 H), 3.97 (s, 3H), 4.21 (d, 2H), 7.55 (dd, 1 H), 7.98 (d, 1 H), 8.09 (dd, 1 H), 8.35 (d, 1 H), 8.58 (dd, 1 H).LCMS (Method A5) Rt 1 .83 min, MS m/z 400 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1289093-31-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

To a 4-Chloro-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (3.08 g, 9.40 mmol, 1.05 equiv) in 40 mL of isopropyl alcohol solution was added 3-Chloro-4-(pyridin-2-ylmethoxy)phenylamine (2.10 g, 9.0 mmol, 1 equiv) at rt. 4 N HCl in dioxane (0.1 mL) was added to the reaction mixture to accelerate the reaction. The reaction mixture was heated at 80 C. for 16 h. The mixture was allowed to cool to rt then filtered and washed with IPA (50 mL). DCM (100 mL) and sat. sodium bicarbonate (100 mL) were added to the solid. The mixture was stirred at rt for 1 h before separated the layers. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4.50 g of crude material. The crude material was purified by flash chromatography (50% THF/DCM) to yield a light yellow (3.60 g, 6.87 mmol, 76%) as product. 1H-NMR (DMSO-d6) delta 9.32 (broad s, 1H), 8.67 (d, J=4.0 Hz, 1H), 8.40 (s, 1H), 8.27 (s, 1H), 8.05 (t, 1H), 7.79 (d, J=2.7 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53 (t, 1H), 7.24 (d, J=8.9 Hz, 1H), 5.35 (s, 2H), 4.66 (s, 2H), 3.66 (t, 2H), 3.19 (t, 2H), 1.43 (s, 9H); LCMS RT=3.39 min, [M+H]+=524.0.

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, 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, 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, name: 1-(6-Nitropyridin-3-yl)piperazine, blongs to pyridine-derivatives compound. name: 1-(6-Nitropyridin-3-yl)piperazine

General procedure: A mixture of compounds 8c-8e (26.0 mmol) in acetic acid(10 mL) and methyl alcohol (40 mL) was refluxed, iron (78.0 mmol)was added. The reaction mixture was heated at 60 C for 2 h. Thereaction mixture was poured into saturated aqueous sodium carbonate(100 mL) and extracted with ethyl acetate (3 x 50 mL), thendried over sodium sulfate, filtered and concentrated. The crudeproduct was purified via column chromatography to afford compounds9c-9e.4.1.11.1. 5-(piperazin-1-yl)pyridin-2-amine (9c). White solid. Yield:68%; 1H NMR (DMSO-d6, 400 MHz) delta: 7.62 (d, J = 2.7 Hz, 1H, Pyr-H),7.17 (dd, J = 8.9, 3.0 Hz, 1H, Pyr-H), 6.40 (d, J = 8.8 Hz, 1H, Pyr-H),5.44 (s, 2H, -NH2), 3.43 (t, J = 4.0 Hz, 4H, Pyr-NCH2CH2N), 2.85 (t,J = 4.0 Hz, 4H, Pyr-NCH2CH2N). 13C NMR (DMSO-d6, 100 MHz):delta 163.0, 162.6, 149.4, 146.9, 133.7, 122.1, 120.3, 43.4, 42.6; HRMS(ESI): calcd for C9H14N4O, [(M+H)+], 179.1297, found 179.1285.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Hui; Hu, Xiaoxia; Cao, Kai; Zhang, Yue; Zhao, Kuantao; Tang, Chunlei; Feng, Bainian; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 935 – 945;,
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 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H3BrF3N

A 5mL microwave vial flushed with Argon was charged with 2-bromo-4-(trifluoromethyl)pyridine (0.0923 mL, 0.724 mmol), 5-cyclopropyl-2-[3-ethylsulfonyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl )-2-pyridyl]-3-m ethyl-6-(trifluoromethyl)im idazo[4 , 5-c]pyrid in-4-one (Step A, 0.2 g), tetrakis(triphenylphosphine) palladium(0) (0.042 g, 0.036 mmol), potassium phosphate tribasic (0.48 g, 2.17 mmol), toluene (2.9 mL) and water (2.9 mL). The mixture was then heated 30 at 110°C under microwave. The reaction mixture was diluted with water and ethyl acetate then, after separation of the phases, the aqueous phase was extracted two time with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated under vacuum. The residue was subjected to columnchromatography over silica gel, eluting with ethyl acetate cyclohexane. The selected fractions were evaporated to yield the title compound as a white solid (0.11 g). 1H NMR (400 MHz, CDCI3) oe ppm 1.08 (m, 2H), 1.30 (m, 2H), 1.40 (t, 3 H), 3.11 (m, 1 H), 3.85(q, 2 H), 4.09 (s, 3 H), 7.20 (s, 1 H), 7.65 (d, 1 H), 8.11 (s, 1 H), 9.00 (d, 1 H), 9.11 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 175205-81-9.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; MUEHLEBACH, Michel; HALL, Roger, Graham; (106 pag.)WO2017/89190; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82671-06-5, Adding some certain compound to certain chemical reactions, such as: 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid,molecular formula is C6H2Cl2FNO2, 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 82671-06-5.

To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 mL), Pd(OAc)2 (0.05 eq, 2.7 g, 11.9 mmol), PPh3 (0.1 eq, 6.2 g, 23.8 mmol), and degassed Et3N (6 eq, 200 mL, 1428.6 mmol). The mixture was stirred for 20 minutes, HCOOH (3 eq, 28 mL, 714.3 mmol) was then added. 5 minutes later, 2,6-dichloro-5-fluoronicotinic acid (50 g, 238.1 mmol) was added. The mixture was stirred at 50 C. The reaction was followed by analysis (1H NMR) of a worked-up aliquot. When all starting material was consumed (24 h), the mixture was cooled to 0 C. and water (500 mL) was added. After 20 minutes, The mixture was filtered through a pad of Celite that was rinsed with water. The mixture was basified to pH 9 with 30% aq. NaOH and washed with EtOAc (2*). HCl (12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3*). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give 37 g (88%) of a beige solid used in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz): delta 8.16 (dd, 1H); 8.58 (d, 1H).

According to the analysis of related databases, 82671-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2011/20377; (2011); A1;,
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 17282-03-0, name is 3-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 131.4: 3-Bromo-2-methoxy-5-methyl-pyridine To a solution of 3-bromo-2-chloro-5-methylpyridine (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide 5.4M in MeOH (25 mL, 135 mmol) and the mixture was stirred at 65C for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et20 and H20 were added and the phases were separated. The organic layer was washed with H20 and brine, dried (MgS04), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90: 10? 0:100) to afford the title compound. tR: 1.03 min (LC-MS 2).

With the rapid development of chemical substances, we look forward to future research findings about 17282-03-0.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem