Month: September 2021

Application of 71838-16-9,Some common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, molecular formula is C7H6BrI, 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: Method B: To a 10 mL sealed vial was added Cu(OAc)2·H2O (20 mg, 0.1 mmol), N-methoxy-1H-pyrrole-2-carboxamide (14 mg, 0.1mmol), aryl halide (1.0 mmol), aminobenzenethiol (1.2 mmol), KOH (224 mg, 4.0 mmol), PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 15 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 40 mL) and water (40 mL). The combined organic phases were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
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Application of 101066-87-9, The chemical industry reduces the impact on the environment during synthesis 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

Step C. 4-(lH-pyrazol-4-yl)-2-(trifluoromethyl)benzonitrile A mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH-pyrazole (CAS: 269410- 08-4, Sigma- Aldrich) (300 mg, 1.55 mmol), 4-iodo-2-(trifluoromethyl)benzonitrile (300 mg, 1.01 mmol), Pd(PPh3)4 (18.6 mg, 0.016 mmol), K2C03 (891 mg, 6.46 mmol), and water (2 mL) in 1 ,4-dioxane (10 mL) under nitrogen was heated at 90 C overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether :EtO Ac (1 : 1) as eluting solvents to afford 4-(lH-pyrazol-4-yl)-2-(trifluoromethyl)benzonitrile as a white solid (203 mg, 84%). LCMS (ESI) m/z: 238.1 [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, 4-Iodo-2-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEAUFOUR-IPSEN (TIANJIN) PHARMACEUTICAL CO., LTD.; AUVIN, Serge; LANCO, Christophe; DUTRUEL, Oliver; CHAO, Qi; GU, Kaichun; WO2015/100617; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 58313-23-8, The chemical industry reduces the impact on the environment during synthesis 58313-23-8, name is Ethyl-3-iodobenzoate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.18. Ethyl 3-(1-(1,3-dioxoisoindolin-2-yl)-4-oxo-4-(quinolin-8-ylamino)butan-2-yl)benzoate (8u). The compound 8u was obtained after purification by column chromatography on silica gel (EtOAc:hexane 40:60) as a colourless solid (59 mg, 77%); Rf (40% EtOAc/hexane) 0.3; mp: 142-144 C; IR (DCM): 3054, 2986, 1713, 1266, 743 cm-1; 1H NMR (400 MHz, CDCl3): dH 9.72 (1H, br. s), 8.80-8.79 (1H, m), 8.45 (1H, d, J 7.5 Hz), 8.12-8.10 (2H, m), 7.92 (2H, d, J 7.6 Hz), 7.67-7.62 (3H, m), 7.56 (2H, dd, J1 5.6, J2 3.0 Hz), 7.46-7.33 (4H, m), 4.37 (2H, q, J 7.1 Hz), 4.10-3.97 (3H, m), 3.08-2.97 (2H, m), 1.39 (3H, t, J 7.1 Hz); 13C NMR (CDCl3, 101 MHz): dC 168.9, 168.3, 166.4, 148.1, 141.3, 138.1, 136.2, 134.1, 133.8, 132.6, 131.8, 131.0, 128.8, 128.6, 127.7, 127.2, 123.1, 121.6, 121.4, 116.2, 61.0, 43.1, 41.8, 40.8, 14.4; HRMS (ESI) calcd for C30H26N3O5 [MH] 508.1872 found 508.1847.

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, Ethyl-3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tomar, Radha; Bhattacharya, Debabrata; Babu, Srinivasarao Arulananda; Tetrahedron; vol. 75; 17; (2019); p. 2447 – 2465;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13194-68-8, name is 4-Iodo-2-methylaniline, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H8IN

Example 14; Preparation of 1-(Tetrahydro-2H-pyran-2-yl)-5-(3,3,3-trifluoroprop-1-yn-1-yl)-1H-indazole (Intermediate 28)Step 1: 5-Iodo-1H-indazole To a solution of 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in CH3CO2H (40 mL), were added NaNO2 (0.39 g, 5.65 mmol) and water (1 mL) at 10 C. The resulting mixture was stirred at room temperature for 6 hours. Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0-40% EtOAc in petroleum ether) affording the title compound (0.90 g). 1H NMR (DMSO-d6, 400 MHz): delta 13.23 (br, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.57 (d, 1H), 7.41 (d, 1H).

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aragon Pharmaceuticals, Inc.; US2012/71535; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 3268-21-1, name is 1,4-Diiodo-2,3,5,6-tetramethylbenzene, belongs to iodides-buliding-blocks compound, 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 3268-21-1, HPLC of Formula: C10H12I2

To a solution of 1 (3.02 g, 7.82 mmol, 1 equiv), Pd(PPh3)2Cl2 (0.380 g, 0.541 mmol, 0.07 equiv) and CuI (0.101 g, 0.530 mmol, 0.07 equiv) in Et2NH was added ethynyltrimethylsilane (2.45 mL, 17.3 mmol, 2.2 equiv) and the reaction was stirred at RT overnight. The solvent was evaporated followed by extraction with CH2Cl2 (3 >< 100 mL) and washing of the organic layer with H20 (2 >< 200 mL) and brine (250 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The product was (0279) purified via column chromatography (PE) leading to 2 as off-white crystals (82%). 1H NMR (400 MHZ, CDClg) 6 2.38 (s, 12H), 0.27 (s, 18H). 13C NMR (400 MHZ, CDC13)8 136.0, 123.4, 104.2, 103.2, 18.5, 0.27. IRV 2957, 2138, 1270, 1073, 863 cm-1. HRMS (EI+) m/z caIcuIated for C20H30Si2 326.1886, found 326.1870. 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. Reference:
Patent; STICHTING VOOR DE TECHNISCHE WETENSCHAPPEN; UNIVERSITEIT VAN AMSTERDAM; RICHELLE, Gaston Julia Johannes; STREEFKERK, Dieuwertje Emma; VAN MAARSEVEEN, Jan Herman; TIMMERMAN, Peter; (162 pag.)WO2018/106112; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, molecular formula is C7H9ClIN, 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. Quality Control of (4-Iodophenyl)methanamine hydrochloride

2,4-dichloro-5-methylpyrimidine (0.300 g, 1.84 mmol) and 4- iodobenzylamine, HC1 (0.496 g, 1.84 mmol) were dissolved in chloroform (4 mL). Triethylamine (0.770 mL, 3.00 mmol) was added and the sealed tube was heated at 60 C overnight. The reaction was purified directly by flash column chromatography (gradient elution with 0- 100% ethyl acetate/hexane) to yield pure 2-chloro-5-methyl-N-(4- iodobenzyl)pyrimidin-4-amine (0.365 g, 1.02 mmol, 55%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59528-27-7, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; UNIVERSITY OF DELAWARE; MALONEY, David J.; ROSENTHAL, Andrew S.; JADHAV, Ajit; DEXHEIMER, Thomas S.; SIMEONOV, Anton; ZHUANG, Zhihao; LIANG, Qin; LUCI, Diane K.; WO2014/105952; (2014); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 69113-59-3, These common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, 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: Palladium Catalyzed Heck Reaction (Conventional Heating) Sodium acetate (3 mmol), substituted piperazine (1.5 mmol), iodo-benzene or bromo-benzene (1 mmol) and tetrabutylammonium chloride (2 mmol) were dissolved in dimethylacetamide (7 mL) and stirred until all reagents dissolved. Palladium(II) acetate (0.25 mmol) was added and the reaction mixture was stirred at 100 C. for 24 h. The reaction mixture was then cooled to room temperature, diluted with dichloromethane and quenched with water. The organic phase was dried, filtered and concentrated in vacuo, then chromatographed in ethyl acetate in hexanes to yield the desired product.; The following compounds were made in this manner: Example Structure Name Yield 14.1 2-{4-[(2E)-3-(3-cyanophenyl)prop-2- enoyl]piperazine-1-yl}nicotinonitrile 53%

Statistics shows that 3-Iodobenzonitrile is playing an increasingly important role. we look forward to future research findings about 69113-59-3.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/49578; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-75-9, name is 2-Iodoacetonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Iodoacetonitrile

General procedure: Starting amine (5.0 mmol) was dissolved in dry diethyl ether (17 mL) and iodoacetonitrile (5.5 mmol, 919 mg) was added dropwise under cooling. The mixture was stirred at room temperature for 3-14 days, then precipitate was filtered off, washed with diethyl ether and dried in vacuo to give the corresponding quaternary ammonium salt 2. If the solid precipitate was not formed after 7 days, the mixture was evaporated under reduced pressure. The crude product was washed with diethyl ether (3 × 15mL) and dried in vacuo. The quaternary ammonium salt 2 was used in the next step without additional purification. The corresponding quaternary ammonium salt (3.0 mmol) was heated at 150 C on oil bath in freshly distilled DMF (7 mL) in a 25 mL round-bottom flask fitted with reflux condenser and CaCl2-tube for 15 minutes. The mixture was cooled to room temperature, diluted with H2O (20 mL) and extracted with PhMe (2 × 15mL). The organic phase then was washed with H2O (2 × 15mL) and brine (15 mL), dried over Na2SO4 and evaporated in vacuo to give the desired aminoacetonitrile 4. The latter, if necessary, was purified by column chromatography (it is convenient to visualize aminoacetonitriles on TLC-plate by treating with the diluted solution of ninhydrin in EtOH). Note, that aminoacetonitriles are moisture sensitive. Products after column chromatography were additionally dried by the addition of dry PhMe (5 mL) and evaporation in vacuo.

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buev, Evgeny M.; Smorodina, Anastasia A.; Stepanov, Maxim A.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 17; (2018); p. 1638 – 1641;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Iodo-4-methoxy-2-nitrobenzene

To a stirred solution of 4-iodo-3-nitroanisole (6.33 g, 22.7 mmol) in acetic acid (3.78 mL) and anhydrous EtOH (37.8 mL) were added Fe (7.60 g, 0.136 mol) and FeCl3 (2.21 g, 13.6 mmol) portionwise at room temperature, and then the mixture was heated to 80 C. After 40 min, the reaction mixture was filtered through a pad of Celite. To the resulting mixture was added H2O and the aqueous layer was extracted with EtOAc three times. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified with flash column chromatography on silica gel (hexane/EtOAc=7/1) to afford 69 (4.77 g, 19.2 mmol, 84%) as a slightly yellow solid. Mp 33-34 C; IR (neat, cm-1) 3459, 3364, 2936, 1613, 1569, 1486, 1428, 1332; 1H NMR (CDCl3, 400 MHz) delta 7.47 (d, J=8.7 Hz, 1H), 6.32 (d, J=2.8 Hz, 1H), 6.13 (dd, J=8.7, 2.8 Hz, 1H), 4.06 (s, 2H), 3.74 (s, 3H); 13C NMR (CDCl3, 100 MHz) delta 161.1, 147.6, 139.2, 106.6, 100.5, 73.4, 55.3; HRMS (DART) calcd for C7H9INO ([M+H]+) 249.9729, found 249.9738.

According to the analysis of related databases, 58755-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yamakawa, Takayuki; Ideue, Eiji; Iwaki, Yuzo; Sato, Ayumu; Tokuyama, Hidetoshi; Shimokawa, Jun; Fukuyama, Tohru; Tetrahedron; vol. 67; 35; (2011); p. 6547 – 6560;,
Iodide – Wikipedia,
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