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 926293-55-2, name is 6-Bromo-2-methylnicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6BrNO

A mixture of 6-chloro-2-methyl-pyridine-3-carbaldehyde (715 mg, 4.60 mmol), methyl 4-hydroxyphenylacetate (694 mg, 4.18 mmol) and K2CO3 (404 mg, 2.92 mmol) in DMF (8.4 mL) was heated to 130 0C for 1 h then filtered and concentrated. The residue was dissolved in EtOAc (40 mL) and washed with brine (3 x 10 mL) then dried (MgSO4) and EPO concentrated. Purification by chromatography on silica gel (30% EtOAc/hexanes) gave [4-(5- formyl-6-methyl-pyridin-2-yloxy)-phenyl]-acetic acid methyl ester as a yellow oil (687 mg, 58%). 1H NMR (CDCl3) delta 2.75 (s, 3H)5 3.66 (s, 2H), 3.73 (s, 3H), 6.76 (d, IH, J= 8.7 Hz), 7.13 (d, 2H, J= 8.7 Hz), 7.34 (d, 2H, J= 8.7 Hz), 8.09 (d, IH, J= 8.4 Hz), 10.24 (s, IH).

With the rapid development of chemical substances, we look forward to future research findings about 926293-55-2.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.Formula: C5H5IN2

To a mixture of 4-iodopyridin-3-amine (40 g, 182 mmol) and ethyl acrylate (27 g, 272 mmol) in DMF (300 mL), DIPEA (28 g, 218 mmol) was added. Then Pd(OAc)2 (4 g, 18 mmol) and P(o-tol)3 (11 g, 36 mmol) were added quickly under N2 atmosphere. The mixture was stirred at 85 C for 12 h under N2 atmosphere. After cooling down, the solvent was removed under reduced pressure. The residue was purified by silica gel column (DCM/ MeOH = 20/1) to give ethyl (E)-3-(3-aminopyridin-4-yl)acrylate (20 g, yield: 57%) as a yellow oil. ESI-MS (M+H): 193.1. ?H NMR (400 MHz, CDC13) (5: 8.15 (s, 1H), 8.02-7.98 (m, 1H), 7.72 (d, J= 16.4 Hz, 1H), 7.18 (d, J= 5.2 Hz, 1H), 6.48 (d, J= 16Hz, 1H), 4.27 (q, J= 7.2 Hz, 2H), 4.07 (s, 2H), 1.34 (t, J= 7.2Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (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. 1186647-69-7, name is 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H3ClIN3, 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: 1186647-69-7

Intermediate 44-Chloro-3-iodo- 1-(4-methoxy-benzyl)~ 1 H-pyrazolo[4, 3-c]pyridine To a mixture of Intermediate 3 (1 g, 3.6 mmol) and KOH (0.3 mg, 5.4 mmol) in DMF (10 ml) at room temperature was added 4-methoxybenzyl chloride (0.5 ml, 3.6 mmol). The resulting mixture was stirred at room temperature for 2.5 h, and then evaporated to dryness. The crude residue was dissolved in EtOAc and washed with water. The organic phase was dried and purified by flash chromatography, eluting with 0 to 30% ethyl acetate/petroleum ether gradient to give a 9:1 mixture of regioisomers as a solid (1.3 g, 93%). Major regioisomer: 1H NMR (400 MHz, DMSO-dB) delta ppm 3.72 (s, 3 H), 5.62 (s, 2 H), 6.85 – 6.94 (m, 2 H), 7.20 – 7.27 (m, 2 H), 7.95 (d, J=6.0 Hz, 1 H), 8.20 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 400 [M + H]+.

With the rapid development of chemical substances, we look forward to future research findings about 1186647-69-7.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; GENENTECH INC.; CHAN, Bryan; CHEN, Huifen; ESTRADA, Anthony; SHORE, Daniel; SWEENEY, Zachary; McIVER, Edward; WO2012/38743; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 96568-04-6 , The common heterocyclic compound, 96568-04-6, name is Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, molecular formula is C10H8Cl2FNO3, 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.

General procedure: 4.1.4.1. 5-(2,6-Dichloro-5-fluoropyridin-3-yl)-3-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (17)A solution of intermediate 5a (0.227 g, 1 mmol) and ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (0.28 g, 1 mmol) in acetic acid (8 ml) was added to a teat glass (40 ml) of Syncore Reactor, keeping the temperature at 125 C and the rotational speed of the device at 300 rpm for 4 h. After this period, the solvent of reaction was concentrated to half under reduced pressure by Syncore Polyvap, and cooled to about 15 C gradually. The mixture was filtered and the solid was washed with acetic acid and water to pH 7, to obtain the compound 17 (0.35 g, Yield: 80%, Purity: 98% by HPLC-DAD) as a white floccular solid. mp >300 C; ESI-Ms (m/z): 443.2 [M + H]+; 1H NMR (500 MHz, DMSO-d6) delta: 7.52 (m, 3H, Ph-H), 7.47 (m, 2H, Ph-H), 6.17 (s, 1H, 6-CH), 8.41 (d, 1H, J = 8, pyridine 4-CH), 12.90 (brs, 1H, NH); 13C NMR (125 MHz, DMSO-d6) delta: 99.33 (6-CH), 104.56 (3-C), 155.63 (7-CO), 152.57, 154.63 (5-C), 140.75 (2-C), 130.65 (Ph-C), 129.22 (Ph-C), 128.89 (Ph-C), 127.94 (Ph-C), 122.86 (CF3), 146.91 (pyridine-C), 142.59 (pyridine-C), 137.94 (pyridine-C), 130.44 (pyridine-C), 130.26 (pyridine-C); HRMS (ESI) calcd for C18H9Cl2F4N4O ([M + H]+), 443.0090; found 443.0085; IRvmax (KBr):1701 (CO), 1629, 1558, cm-1.

The synthetic route of 96568-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qi, Jinlong; Zhang, Fan; Mi, Yi; Fu, Yan; Xu, Wen; Zhang, Diqun; Wu, Yibing; Du, Xiaona; Jia, Qingzhong; Wang, Kewei; Zhang, Hailin; European Journal of Medicinal Chemistry; vol. 46; 3; (2011); p. 934 – 943;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 870997-85-6, 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.870997-85-6, name is 3-Amino-5-bromopyridine-2-carboxylic Acid, molecular formula is C6H5BrN2O2, molecular weight is 217.0201, as common compound, the synthetic route is as follows.

Step 1: 3-Amino-5-(4-trifluoromethoxy-phenylsulfanyl)-pyridine-2-carboxylic acid: [00273] A solution of 3-amino-5-bromo-pyridine-2-carboxylic acid (Int 1, 3.26 g, 15 mmol), 4- trifluoromethoxy-benzenethiol (CAS: 169685-29-4, 3.5 g, 18 mmol) and DBU (2.22 mL, 15 mmol) was prepared in DMA (15 mL). This mixture was heated at 140 C for 45 minutes in a microwave reactor. Next, the mixture was diluted with a mixture of 1% AcOH in water. A suspension was obtained that was subsequently filtered. This collected solid was washed with a 101 ABV12212USO1 1% AcOH/water mixture followed by washing with petroleum ether. After drying in a vacuum oven, the titled compound was obtained

The chemical industry reduces the impact on the environment during synthesis 870997-85-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 88511-27-7, 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.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 4-amino-3-iodopyridine(1) (220 mg, 1.00 mmol), tert-butylamine (0.315 mL, 3.00 mmol)(or the given amount of primary or secondary amine (Table 1)) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL autoclave. The atmosphere was changed to carbonmonoxide and pressurized to 40 bar. The reaction was conducted for the given reaction time upon stirring at 50C and analysed by TLC. The autoclave was vented, the reaction mixture was concen-trated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (320 mL). The organic phase was dried over Na2SO4, filtered and evaporated to a solid material. All compounds were subjected to column chromatography ((Silicagel 60 (Merck), 0.063 e 0.200 mm); MeOH/CHCl3 orMeOH/EtOAc/CHCl3 (the exact ratios are specied in Characterization (4.4.) for each compound)).

Statistics shows that 88511-27-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3-iodopyridine.

Reference:
Article; Szoke, Gyoengyi; Takacs, Attila; Berente, Zoltan; Petz, Andrea; Kollar, Laszlo; Tetrahedron; vol. 72; 22; (2016); p. 3063 – 3067;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 137178-88-2 ,Some common heterocyclic compound, 137178-88-2, molecular formula is C6H3BrClNO, 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 stirred solution/suspension of 5-bromo-2-pyridinecarboxylic acid (0.2 g, 1 mmol) in CH2Cl2 (25 mL) was added oxalyl chloride (0.26 mL, 3 mmol) and 1 drop of DMF. Gas evolved and the all the solids dissolved. After Ih the reaction was evaporated and pumped. This material was dissolved/suspended in CH3CN (10 mL) then Intermediate C (0.25 g, 1 mmol) and diisopropylethylamine (2 mL) were added. A white solid formed(DIEA.HCl). After 1.5 h the reaction was filtered and the filtrate was evaporated, taken up in CH2Cl2, filtered and chromatographed on silica gel, eluting with a gradient of 0-10% methanol +1% ammonium hydroxide in CH2CI2. The product fractions were evaporated, dissolved in CBD2CI2, washed with 1 M NaOH (to remove residual hydrochloride salt) and evaporated to afford 0.25g of 24A (58% yield). 1H NMR (300 MHz, DMSOd5) 69.30 (t, /= 6.4 Hz, IH), 8.78 (d, J= 2.1 Hz, IH), 8.25(dd, J= 2.3 Hz, J= 8.2 Hz, IH), 7.98 (d, J= 8.3 Hz, IH), 7.19 (t, J= 7.8 Hz, IH), 6.88 – 6.80 (m, 2H), 6.74 – 6.68 (m, IH), 4.50 (t, J= 4.9 Hz, IH), 4.43 (d, J= 6.4 Hz, 2H), 3.03 – 2.96 (m, 2H), 2.52 – 2.47 (m, 3H), 2.03 – 1.87 (m, 6H), 1.77 – 1.68 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137178-88-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/78251; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 159870-80-1, name is 5-Fluoro-2-iodopyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H3FIN

General procedure: Pyridines substituted at the 2-position with halides shown in Tables 2 and 3 are stirred in a mixture of toluene (900 mL) and anhydrous ether (600 mL). The resulting solutions were cooled to < -100 C for 20 min at which point n-BuLi/hexane was added slowly over 22 min. After maintaining the temperature below -100 C for 20 min, triisopropylborate was added dropwise, and then the reaction mixture was stirred below -70 C. After stirring for 4 h, ether (500 mL) was added and the solution was allowed to stand overnight at room temp. Isopropanol was added (30mL), then the reaction mixture was stirred for 30 min, the allowed to stand without stirring for an additional 2 h. The resulting precipitate was collected by filtration then washed with ethyl ether and dried under nitrogen atmosphere for 1.5 h. The resulting triisopropoxy analog was treated with a mixture of acetone and water (450 mL/50 mL) to remove any contaminating n-butylborate lithium salt. The solids were collected by filtration, washed with acetone/water (9:1, 300 mL), and dried in air for 2h, then lyophilized overnight to afford product. The synthetic route of 159870-80-1 has been constantly updated, and we look forward to future research findings. Reference:
Article; Chen, Kuanchiang; Peterson, Richard; Math, Shivanand K.; Lamunyon, James B.; Testa, Charles A.; Cefalo, Dustin R.; Tetrahedron Letters; vol. 53; 36; (2012); p. 4873 – 4876;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-86-7, Adding some certain compound to certain chemical reactions, such as: 153034-86-7, name is 2-Chloro-4-iodopyridine,molecular formula is C5H3ClIN, 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 153034-86-7.

To a solution of of 2-chloro-4-iodopyridine (1.0 g, 4.18 mmol) in anhydrous THF (10 mL) was added n-BuLi (3.34 mL, 8.35 mmol) at -78 C. The mixture was stirred at -78 C for 20 mins. Then oxetan-3-one (361 mg, 5.01 mmol) was added at -78 C and the mixture was stirred at -78 C for 50 mins. The mixture was quenched with saturatedNH4Cl (10 mL) and extracted with ethyl acetate (100 mL><3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford the crude product, which was purified on silica gel chromatography (EA: PE = 5% ~ 40%) to afford3-(2-chloropyridin-4-yl)oxetan-3- ol(620 mg, yield 86%) as a yellow solid.(ESI): M/Z (M+l): 352 (Condition: 0- 60AB 3MIN; R.T.: 1.303). 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. 153034-86-7, 2-Chloro-4-iodopyridine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73290-22-9, Adding some certain compound to certain chemical reactions, such as: 73290-22-9, name is 2-Bromo-5-iodopyridine,molecular formula is C5H3BrIN, 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 73290-22-9.

Pd2(dba)3 (229 mg, 0.25 mmol), Xantphos (290 mg, 0.5 mmol) and sodium tert-butoxide (2.88 g, 30 mmol) were added to 2-bromo-5-iodopyridine (3.41 g, 12 mmol)And a solution of 1-methylpiperazine (1.0 g, 10 mmol) in toluene (50 ml), heated to 60 degrees Celsius under the protection of argon, and stirred for 24 hours.After the reaction solution was cooled to room temperature, the solid was filtered off, the filter cake was washed with ethyl acetate, and the filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by Combi-flash column chromatography [DCM: MeOH = 100: 0 to 90:10] The compound 1-(6-bromopyridin-3-yl)-4-methylpiperazine was obtained (2.68 g, 79.3%).

According to the analysis of related databases, 73290-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Zhou Fusheng; Shi Xiaoyong; Huang Dong; Tang Wangqi; Wang Shengyuan; Zhao Jinzhu; Qiao Changjiang; Chen Xi; Lan Jiong; (28 pag.)CN110256446; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem