Tag: M.W:100-200

Electric Literature of 1702-18-7 ,Some common heterocyclic compound, 1702-18-7, molecular formula is C6H2Cl2N2, 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 1 Preparation of 6-chloro-3-methylthio-2-pyridinecarbonitrile and 3-chloro-6-methylthio-2-pyridinecarbonitrile 69.2 Grams (g) of 3,6-dichloro-2-pyridinecarbonitrile was dissolved in 250 milliliters (ml) of THF and chilled to about 10 C. Methanethiol (19.2 g) was added and the whole mixture was cooled to about 5 C. While the temperature was maintained at about 0 to 5 C., 44.9 g of t-BuOK in 550 ml of THF was added slowly. After the addition of t-BuOK was complete, the reaction mixture was allowed to warm to room temperature, and was stirred for 3 hours and then poured onto ice, forming a precipitate which was collected by filtration. The precipitate was dissolved in CH2 Cl2, dried, concentrated and diluted with hexane to give 24.7 g of white crystalline material which was subsequently identified by NMR to be 6-chloro-3-methylthio-2-pyridinecarbonitrile. The filtrate from the above-described filtration was then concentrated leaving a solid which was recrystallized twice and filtered (retaining the filtrates after each recrystallization). The solid obtained was identified as 6-chloro-3-methylthio-2 -pyridinecarbonitrile (14.5 g). The retained filtrates were combined and concentrated to give 17.5 g of a mixture of 6-chloro-3-methylthio-2-pyridinecarbonitrile and 3-chloro-6-methylthio-2-pyridinecarbonitrile in a ratio of about 3:1, respectively. The isomers were then separated on a Waters Prep LC500 instrument using 15% ethyl acetate in hexane. The melting point of the 6-chloro-3-methylthio-2-pyridinecarbonitrile isomer was found to be 115-118 C., while 3-chloro-6-methylthio-2-pyridinecarbonitrile was found to have a melting point (m.p.) of 76-80 C.

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. 1702-18-7, 3,6-Dichloropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Dow Chemical Company; US4558134; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 108281-79-4, 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. 108281-79-4, name is 6-Bromo-[1,2,4]triazolo[4,3-a]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.

In a 5 mL vial 6-bromo-[1,2,4]triazolo[4,3-a]pyridine (93 mg), 4-trifluoromethoxyphenylboronie acid (115 mg), and potassium carbonate (187 mg) were suspended in DMF (2 mL) that was previously degassed with nitrogen. Tetrakis(triphenylphosphine) palladium (20 mg) was added and the reaction mixture was heated in a microwave reactor at 150 C. for 30 min, filtered, and concentrated. The residue was subjected to gradient chromatography (MeOH/dichloromethane) to produce white powder, 56.4 mg (43% yield).1H NMR (400 MHz, CDCl3): delta 8.89 (s, 1H), 8.27 (br s, 1H); 7.89 (d, J=9.2 Hz, 1H); 7.59 (d, J=8.4, 2H); 7.52 (d, J=9.6 Hz, 1H); 7.36 (d, J=7.6, 2H).MS (ES+, m/z) 280.0 (base peak, M+H+); 581.0 (2M+Na+).

According to the analysis of related databases, 108281-79-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Palo Alto, Inc.; US2011/21521; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19337-97-4 ,Some common heterocyclic compound, 19337-97-4, molecular formula is C8H7NO2, 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 mixture of (E)-3-(pyridin-3-yl)acrylic acid (37 mg, 0.25 mmol) in DMF (2 mL) was added EDCI (78 mg, 0.41mmol), HOBt (41 mg, 0.31 mmol), triethylamine (0.06mL, 0.41mmol), and compound 40a (65 mg, 0.2 mmol), and the reaction mixture was stirred for 4 h at room temperature. DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (4 mL × 3). The combined organic layers were washed with saturated aqueous NaHCO3 solution, saturated aqueous NH4Cl solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting mixture was purified by silica column chromatography to give the target compound 19 as white solid (45 mg, 50percent). 1H NMR (400 MHz, CDCl3) delta 8.76 (s, 1H), 8.57 (d, J = 4.2 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 15.7 Hz, 1H), 7.60 (s, 1H), 7.52 (s, 1H), 7.30 (t, J = 9.1 Hz, 3H), 7.23 (d, J = 7.7 Hz, 3H), 7.12 (d, J = 6.5 Hz, 3H), 6.47 (d, J = 15.7 Hz, 1H), 5.78 (s, 1H), 3.37 (dd, J = 13.2, 6.8 Hz, 2H), 2.63 (t, J = 7.3 Hz, 2H), 1.60 ? 1.52 (m, 4H), 1.30 (dt, J = 15.4, 7.6 Hz, 2H). 13C NMR (125 MHz, CDCl3) delta 165.4, 150.3, 149.1, 143.5, 139.1, 137. 7, 136.9, 134.6, 133.1, 130.7, 129.3, 128.9, 127.0, 125.4, 124.7, 123.8, 122.7, 122.1, 39.7, 35.1, 30.2, 29.3, 25.9. HRMS(ESI) m/z calculated for C25H28N3O3S [M + H]+: 450.1846, found 450.1846.

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. 19337-97-4, trans-3-(3-Pyridyl)acrylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Kuojun; Ni, Yong; Chen, Jiaxuan; Tu, Zhengchao; Wu, Xiaoxing; Chen, Dong; Yao, Hequan; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 29; 12; (2019); p. 1502 – 1506;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1990-90-5, Adding some certain compound to certain chemical reactions, such as: 1990-90-5, name is 3-Methylpyridin-4-amine,molecular formula is C6H8N2, 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 1990-90-5.

To a solution of 2-(5-chloro-2-fluorophenyl)-4-iodo-5,7-dihydrofuro[3,4-d]pyrimidine (80 mg, 0.21 mmol, 1 eq) in anhydrous dioxane (5 ml) was added Pd(OAc)2 (2 mg, 0.01 mmol, 0.05 eq) followed by BINAP (10 mg, 0.02 mmol, 0.075 eq), 4-amino-3- picoline (25 mg, 0.23 mmol, 1.2 eq) and Cs2CO3 (100 mg, 0.32 mmol, 1.5 eq). The EPO reaction mixture was heated to 80C for 15h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (9:l/ethyl acetate:hexane) to afford [2-(5-Chloro-2-fluorophenyl)-5,7- dihydrofuro[3,4-d]pyrimidin-4-yl]-(3-methyl-pyridin-4-yl)-amine, compound of formula (33) (20 mg, 26%) as a white solid

According to the analysis of related databases, 1990-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6959-48-4, 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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

General procedure: To a solution of4(1.00 eq.) in DMF was added K2CO3(1.20-2.00 eq.). The reaction was stirred at room temperature for 1 h, followed by the addition of the alkyl halide (1.00-1.10 eq.). The reaction was stirred at room temperature for 0.5-24 h, concentrated under reduced pressure and purified by flash column chromatography (silica gel, solvent system I: petroleum ether ramping to 100% EtOAc, or solvent system II: DCM ramping to DCM/MeOH = 97:3) to give the desired product.

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 6959-48-4, 3-(Chloromethyl)pyridine hydrochloride.

Reference:
Article; Diab, Sarah; Abdelaziz, Ahmad M.; Li, Peng; Teo, Theodosia; Basnet, Sunita K.C.; Noll, Ben; Rahaman, Muhammed H.; Lu, Jingfeng; Hou, Jinqiang; Yu, Mingfeng; Le, Bich T.; Albrecht, Hugo; Milne, Robert W.; Wang, Shudong; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 762 – 772;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, 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.

Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10% EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39% yield). LCMS: 254.8 (M+). Further elution with 12% EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39% yield).

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 14432-12-3, 4-Amino-2-chloropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54221-95-3, 2-Acetylaminoisonicotinic acid, 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, Product Details of 54221-95-3, blongs to pyridine-derivatives compound. Product Details of 54221-95-3

A mixture of (-)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (1.50 g, 5.12 mmol, Amine-1, single enantiomer), 2-acetamidoisonicotinic acid (1.01 g, 5.63 mmol), HBTU (2.33 g, 6.14 mmol) and triethylamine (3.57 mL, 25.6 mmol) in dichloromethane (51 mL) is stirred at room temperature for 15 hours. The reaction mixture is poured into water (50 mL) and extracted with dichloromethane (50 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate to give 1.30 g (66percent yield) of the title compound as a white solid.1H-NMR (300 MHz, DMSO-d6) delta 10.6 (1H, s), 9.08 (1H, d, J = 8.1 Hz), 8.41-8.38 (2H, m), 8.18 (1H, d, J = 2.2 Hz), 7.82 (1H, dd, J = 8.4, 2.2 Hz), 7.43 (1H, d, J = 5.1 Hz), 6.96 (1H, d, J = 8.8 Hz), 5.14 (1H, m), 4.96 (2H, q, J = 9.2 Hz), 2.09 (3H, s), 1.47 (3H, d, J = 7.0 Hz), MS (ESI) m/z: 383 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54221-95-3, 2-Acetylaminoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; ARANO, Yoshimasa; MORITA, Mikio; WO2012/53186; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67346-74-1, 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.67346-74-1, name is 3-Ethynylpyridin-2-amine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

Reference Example 46 3-(3-(4-(5-Methyl-furan-2-ylmethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a mixture of (4-(5-methyl-furan-2-ylmethyl)-phenyl)-acetohydroximoyl chloride (11 mg, 0.043 mmol) described in Manufacturing Example 46-1-6 and tetrahydrofuran (1 mL) were added 3-ethynyl-pyridin-2-ylamine (4.0 mg, 0.034 mmol) described in Manufacturing Example 1-2-3 and triethylamine (9.4 muL, 0.068 mmol) at room temperature, which was stirred for 3 hours at 45 C. The reaction mixture was cooled to room temperature, water was added at the same temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=2:3) to obtain the title compound (5.1 mg, 41%).1H-NMR Spectrum (CDCl3) delta (ppm): 2.24 (3H, s), 3.90 (2H, s), 4.03 (2H, s), 5.53 (2H, br s), 5.85 (1H, d, J=2.9 Hz), 5.87 (1H, d, J=2.9 Hz), 6.26 (1H, s), 6.72 (1H, dd, J=5.0, 7.6 Hz), 7.21 (4H, s), 7.72 (1H, d, J=7.7 Hz), 8.12 (1H, dd, J=1.8, 4.9 Hz).

The chemical industry reduces the impact on the environment during synthesis 67346-74-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2524-52-9, Ethyl 2-picolinate, 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, COA of Formula: C8H9NO2, blongs to pyridine-derivatives compound. COA of Formula: C8H9NO2

To a solution of 73-3 (5.0 g, 1 equiv.) in EtOH (30 mL) was added NH2NH2H2O (2.5 g, 1.5 equiv.). Then the mixture was heated to reflux and stirred for 16 h. The reaction was completed. The reaction mixture was cooled to room temperature and concentrated to get 4.6 g of crude 73-4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2524-52-9, Ethyl 2-picolinate, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY; JACOBS, Robert Toms; LIU, Yang; SCIOTTI, Richard J.; (0 pag.)WO2018/160845; (2018); A1;,
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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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. Recommanded Product: 13466-38-1

A mixture of 5-bromopyridin-2-ol (I-99, Aldrich, Wis.; 53 g, 0.30 mol) in concentrated.H2SO4 (250 mL) was stirred with ice bath cooling and concentrated HNO3 (105 mL) was added slowly to the mixture. The reaction mixture was stirred for 4 hours at room temperature and then poured onto ice and stirred for additional 30 minutes. A yellow precipitate was filtered off used in the following step without further purification (45 g, 68%). MS (ESI): m/z 220 (M+1)+.

With the rapid development of chemical substances, we look forward to future research findings about 13466-38-1.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem