Month: July 2021

Synthetic Route of 83863-33-6, A common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

A solution of 5-iodo-2-methylaniline (1g, 42.91mmol) and 2-tert butyldicarbonate (1.03g, 47.19 mmol) in THF (10 ml) was stirred at reflux temperature for 2 hours. Solvent was then removed in vacuo, the residue dissolved in ethyl acetate and this solution was washed successively with 1M citric acid solution and brine. The organic phase was dried over MgSO4 and concentrated in vacuo. The resultant yellow-white solid was crystallized from hexane to give white solid 2 (1.22 g, 85.3%).

The synthetic route of 83863-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Raju, Gheevarghese; Capo, Joseph; Lichtenstein, Bruce R.; Cerda, Jose F.; Koder, Ronald L.; Tetrahedron Letters; vol. 53; 10; (2012); p. 1201 – 1203;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 20691-72-9, name is 4-Iodo-2-nitroaniline, 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 20691-72-9, Quality Control of 4-Iodo-2-nitroaniline

Method a To a solution of diphosgene (4.1 mL, 34.1 mmol) in EtOAc (40 mL) at 0 C. was added a solution of the 4-iodo-2-nitroaniline (45.5 mmol) in EtOAc (200-500 mL), and the mixture was heated to reflux for 18 h. The solvent was removed in vacuum to leave a brown solid, which was triturated with hot hexane (200 mL). The solid material was filtered off and the filtrate was concentrated under reduced pressure to leave the pure 4-iodo-2-nitrophenylisocyanate as a yellow solid.

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6509328; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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.

[C.] [N- (6-NITROQUINOLIN-4-YL)-N- (N, N-DIMETHYLAMINOETHYL)-2-IODO-5,] 6- dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3, 4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3 x 75 mL), and extracted with 5 % aqueous HCl (4 x 100 mL). The combined aqueous extracts were basified with 30% [NAOH] and then extracted with chloroform (3 x 100 mL). Combined organic extracts were then dried [(MGSO4)] and evaporated to give 1.15 g of the amide, in 78 % yield ; 1H NMR [(CDC13)] 8 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 [(M,] 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, [1H),] 7.79 (d, 1H, [J=5.] 2), 8.22 (d, [1H,] [J=9.] 2), 8. 48 (d, 1H, J=9. 2), 9.0 (d, 1H, J=5. 2), 9.28 (s, [1H)] ; [13C] NMR [(CDC13)] [5] 45.5, 48.0, 55.6, 56.1, 56. 8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149. 8, 151.5, 154.1, 169.7 ; IR (CHC13) 1345,1535, 1655.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4,5-dimethoxybenzoic acid, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip) belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 11 (65 mg, 0.1 mmol), 1,3-diiodopropane (88.8 mg, 0.3 mmol) was added to an 8 mL vial.DIPEA (diisopropylethylamine, 20 uL), acetonitrile (150 uL), and the reaction mixture was reacted at 80 C for 12 hours.The reaction solution was drained, washed with DCM, washed with saturated aqueousThe solid was washed with diethyl ether to give a white solid compound 12 (40 mg, yield = 38%)

The synthetic route of 1,3-Diiodopropane(stabilized with Copper chip) has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H4F3I

A 50-mL round bottom flask was charged with S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-3-oxopropyl) ethanethioate (1.6 g, 4.54 mmol) and methanol (30 mL) The mixture was purged with a flow of nitrogen for 15 min. Sodium methoxide (0.735 g, 13.6 mmol) was added, and the suspension was stirred under nitrogen for 5 min. 1,1,1-Trifluoro-3-iodopropane (1.6 mL, 13 6 mmol) was added and the reaction was heated at 50 C. for 4 h, at which time HPLC analysis revealed complete conversion of S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-3-oxopropyl) ethanethioate to product. The reaction was cooled to room temperature and transferred to a separatory funnel and EtOAc (100 mL) and water (50 mL) were added. The layers were separated and the aqueous phase was extracted with EtOAc (50 mL) The combined organic layers were washed with brine (25 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography (20-100% EtOAc/hexanes) to afford an oil which solidified to give the desired product as a white solid (1.52 g, 82% yield, 97% HPLC purity). mp 79-80 C. 1H NMR (400 MHz, CDCl3): 8.94 (s, 1H), 8.62 (d, J=4.6 Hz, 1H), 8.04(d, J=9.3 Hz, 1H), 7.97 (s, 1H), 7.45 (m, 1H), 3.70 (q, J=7.0 Hz, 2H), 2.83 (t, J=7.2 Hz, 2H), 2.70-2.57 (m, 2H), 2.43 (t, J=7.2 Hz, 2H), 2.40-2.27 (m, 2H), 1.15 (t, J=7.1 Hz, 3H). ESIMS m/z 406.9 ([M+H]+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 460-37-7.

Reference:
Patent; Dow AgroSciences LLC; YANG, Qiang; LORSBACH, Beth; NIYAZ, Noormohamed M.; BUYSSE, Ann M.; WALSH, Martin J.; Zhang, Yu; TRULLINGER, Tony K.; MOLITOR, Erich J.; CANTURK, Belgin; HAO, Yan; KISTER, Jeremy; (23 pag.)US2018/186753; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 6940-76-7, name is 1-Chloro-3-iodopropane, 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 6940-76-7, HPLC of Formula: C3H6ClI

A reaction flask was charged with 6-fluoro-4H-benzo[ 1.4]oxazin-3-one (1.67 g, 10 mmol), 1-chloro-3-iodopropane(2.04 g, 10 mmol), and Cs2CO3 (4.88 g, 15 mmol) in MeCN (10 mE) and stirred at it for 3 days. The reaction mixture wasquenched with water and the product extracted into EtOAc. The combined organic phases were dried over Na2504,filtered, and concentrated. The product was purified by flashcolunm chromatography (5i02 n-heptane/EtOAc 2:1) togive the title compound (145EH20) (2.32 g, 95%). ?H NMR (CDC13) oe 6.95-6.91 (m, 1H), 6.82-6.78 (m, 1H), 6.72-6.67 (m, 1H), 4.57 (s, 1H), 4.05 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.2Hz, 2H), 2.19-2.11 (m, 2H); ?3C NMR (CDC13) oe 164.6,158.6 (d, J=240.7 Hz), 141.5 (d, J=2.3 Hz), 129.6 (d, J=10.5Hz), 118.0 (d, J=9.3 Hz), 110.0 (d, J=23.1 Hz), 102.7 (d, J=28.8 Hz), 67.8, 42.3, 39.3, 30.0.

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.

Reference:
Patent; ACADIA PHARMACEUTICALS, INC.; Skjaerbaek, Niels; Koch, Kristian Norup; Friberg, Bo Lennart Mikael; Tolf, Bo-Ragnar; (70 pag.)US9522906; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 612-55-5, name is 2-Iodonaphthalene, A new synthetic method of this compound is introduced below., COA of Formula: C10H7I

General procedure: A mixture of aryl halide (1.0 mmol), alkene (1.1 mmol), triethylamine (2 mmol), DMF (5 mL), and the catalyst (30 mg, 0.28 mol% Pd ) was stirred at 80 C for an appropriate time under aerial condition. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, poured into H2O (10 mL), and the catalyst was separated by magnetic decantation. In the case of acrylic acid, aqueous solution of Na2CO3 (10 mL, 3% w/v) was added; after separation of the catalyst, and the product was extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine (2 × 10 mL), dried over MgSO4, and concentrated in vacuum. The crude product was further purified by column chromatography (silica mesh size 60-120).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Vibhute, Sandip P.; Mhaldar, Pradeep M.; Shejwal, Rajendra V.; Rashinkar, Gajanan S.; Pore, Dattaprasad M.; Tetrahedron Letters; vol. 61; 17; (2020);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1643-29-4, 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. 1643-29-4 name is 3-(4-Iodophenyl)propanoic acid, This 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: 3-(4-Iodophenyl)propanoic acid (7)33 (1.0 equiv) was added to SOCl2 (0.2 mmol/mL) under a nitrogen atmosphere. The mixture was refluxed for 1.5 h after which the SOCl2 was evaporated in vacuo. The residue was co evaporated 2 times with toluene and subsequently dissolved in toluene (0.1 mmol/mL). Methyl-2-aminobenzoate or methyl 2-aminothiophene-3-carboxylate (1.4 equiv) was added and the mixture was stirred overnight at room temperature under a nitrogen atmosphere. Upon completion of the reaction, the precipitate was filtered off and the filtrate was concentrated. The obtained residue was purified by column chromatography (Pet. Et/EtOAc 4:1) to give the target compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Iodophenyl)propanoic acid, and friends who are interested can also refer to it.

Reference:
Article; Van Veldhoven, Jacobus P.D.; Liu, Rongfang; Thee, Stephanie A.; Wouters, Yessica; Verhoork, Sanne J.M.; Mooiman, Christiaan; Louvel, Julien; Ijzerman, Adriaan P.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 4013 – 4025;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6940-76-7, name is 1-Chloro-3-iodopropane, 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. Recommanded Product: 1-Chloro-3-iodopropane

General procedure: 1-Boc-piperazine (2 g, 10.74 mmol, 1.0 equiv) was combined with K2CO3 (5 equiv) in DMF (10 mL), followed by 1-Chloro-3-iodoproprane (1.0 equiv) and the mixture was stirred at 50 C for 1 h. The reaction progress was monitored by LC-MS and upon completion of the reaction 4-cyanophenol (1.2 equiv) and sodium iodide (0.1 equiv) was added and the reaction allowed to stir at 70 C for 2 h. The mixture was poured onto water and extracted with EtOAc, washed with brine and dried over Na2SO4. The volatiles were removed under reduced pressure and the crude mixture purified on silica gel (60 – 90 C PE : EtOAc = 3:1) to provide the desired product.

The synthetic route of 6940-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ren, Jing; Xu, Wei; Tang, Le; Su, Minbo; Chen, Danqi; Chen, Yue-Lei; Zang, Yi; Li, Jia; Shen, Jingkang; Zhou, Yubo; Xiong, Bing; Bioorganic and Medicinal Chemistry Letters; vol. 26; 18; (2016); p. 4472 – 4476;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 135050-44-1, 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. 135050-44-1 name is 3-Chloro-4-iodoaniline, This 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.

3-Chloro-4-(4-chlorophenyl)benzenamine A mixture of 3-chloro-4-iodobenzenamine (500 mg, 1.97 mmol), 4- chlorophenylboronic acid (324 mg, 2.07 mmol), Na2CO3 (627 mg, 5.92 mmol) and Pd(PPh3)4 (228 mg, 0.20 mmol) in 1,4-dioxane (21 mL) and H2O (4 mL) was stirred at 80 oC under argon for 16 h. The mixture was allowed to cool to RT and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate / petroleum ether = 5/1) to afford the desired product (424 mg, 91% yield) as a yellow solid.

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

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; WU, Tao; REN, Pingda; LIU, Yi; LIU, Yuan; LONG, Yun, Oliver; WO2015/54572; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com