Month: May 2021

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. 1189352-83-7, name is 3-Chloro-5-iodobenzotrifluoride, A new synthetic method of this compound is introduced below., Formula: C7H3ClF3I

2)9- (4-methoxyphenyl) -10 anthracene boronate 3mmol,1-chloro-3-iodo-5-trifluoromethyl-4,6-dihydrosubstituted benzene 3 mmol,Tetrakis(triphenylphosphine)palladium 0.3 mmol,Toluene 120mL,30 mL of ethanol and 120 mmol of K2CO3 (formed as a solution with 30 mL of distilled water) were added to the reaction flask.Then vacuum the system,Nitrogen protection,The reaction was carried out at 110 C for 24 hours.After the reaction,extraction,Rotary evaporation,Column chromatography (eluent: n-hexane / dichloromethane = 1:1),Recrystallization gave the product A9.The yield was 69%. 3)Will A9 2mmol,Boronic acid pinacol ester 6mmol,Palladium acetate 0.2 mmol,2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl 0.4 mmol,Potassium acetate 6mmol,Add 1,4-dioxane 90mL to the reaction flask,Then vacuum the system,Nitrogen protection,The reaction was carried out at 105 C for 18 hours.After the reaction,extraction,Rotary evaporation,Column chromatography (eluent: n-hexane / dichloromethane = 2:1),Recrystallization to give the product B9,The yield was 68%. 4)The final product i is obtained by Suzuki coupling reaction: B9 1mmol,The product obtained in step 2 is 9-bromo-10-(4-cyano)benzoquinone 0.84 mmol.Catalyst tetrakis(triphenyl)phosphine palladium 0.12 mmol,Toluene 60mL,20mL of ethanol,K2CO3 33.6mmol (formed into solution with 20mL distilled water),Add to the reaction bottle,Under the protection of nitrogen,It was refluxed at 110 C for 24 h.After the reaction, the methanol is hot washed,Filtering,Recrystallization of toluene,Sublimation gives the final product.The yield was 69%.

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:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; Duan Xuewei; (24 pag.)CN109503427; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 773136-66-6, name is Ethyl 2-Fluoro-5-iodobenzoate, 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 773136-66-6, Formula: C9H8FIO2

Under nitrogen atmosphere, starting Ester Intermediate 5e (5.0 g, 15.3 mmol) was dissolved in THF (40 mL), the reaction mixture was cooled to -50C and stirred for 10 minutes. Isopropyl-magnesium-chloride (1 1 mL of a 2M solution in THF) was added dropwise and the reaction mixture was stirred at -50C for 2h. The reaction mixture was cooled to -78C and a solution of cyclobutanone (2.15 g, 30.6 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred at -78C for 1 h, then warmed to room temperature and stirred for 18h. The solvent was removed under vacuum, dichloromethane was added and the reaction mixture was washed with a saturated solution of NaHCO3, The organic phase was concentrated under vacuum and the crude product obtained was purified by flash chromatography (eluent from 90:10 to 80:20 Cy/EtOAc) to obtain the desired product (3.0 g). GC-MS (Method 10): Rt = 10.91 min MS : m/z = 210 (M-28)+

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 2-Fluoro-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FRATTINI, Sara; DI ANTONIO, Giustino; WO2014/19979; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 132131-24-9, 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. 132131-24-9, name is 2-Amino-5-iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Alternative Synthesis of iV-(4-moipholinophenyl)-6-(4-(4-morphoIinophenyIamino)quinazolin-6-yl)quinazolin-4-amine; N’-(2-Cyano-4-iodo~phenyl)-N,N-dimethyl-formamidine:2-Amino-5-iodo-benzonitrile (5g, 20.5mmol) was heated to reflux in DMF-DMA (20ml) for 2h. On cooling and concentrating to dryness in vacuo the residue was filtered through silica (2Og, SiO2) eluting with dichloromethane to afford a brown oil (6.15g, 100%)1H NMR (CDCl3) delta 7.71 ( IH, d), 7.58 ( IH, dd), 7.505 ( IH, s), 6.64 (IH, d), 3.01 (6H, s)LC-MS rt 3.46 m/z 299 MH+; Example 2; N*4*-(4-Morpholin-4-yI-phenyl)-N*4*-phenyl-[6,6′]biquinazolinyl-4,4′- diamine; N’-(2-Cyano-4-iodo-phenyl)-N,N-dimethyl-formamidine; 2-Amino-5-iodo-benzonitrile (5g) in DMF-DMA ( 10ml) was heated to 110 for 2h. The cooled reaction mixture was diluted with water (100ml) and extracted into ethyl acetate (3xl00ml). The combined organic phases were dried (MgSO4) and concentrated to give a viscous brown oil (~ quantitative) which was used without further purification.1H NMR (CDCl3) delta 7.77 (IH, m), 7.65 (IH, dm, J8.85Hz), 7.57 (IH, s), 6.70 ( IH, d,J8.85Hz), 3.012 (6H, s)LC-MS rt 3.46 m/z 299.78

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, 2-Amino-5-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2006/79833; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 845866-78-6, A common heterocyclic compound, 845866-78-6, name is 1-Bromo-3-iodo-5-(trifluoromethoxy)benzene, molecular formula is C7H3BrF3IO, 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: 8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), respective aryl iodide (10.8 mmol), and anhydrous DMF (24 mL) were taken in a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape, heated at 1 10 C, and magnetically stirred for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0223] 8-((3-Bromo-5-(trifluoromethoxy)phenyl)thio)-9H-purin-6-amine (2h). Obtained by method A as a light yellow solid in 41 % yield. MS (ESI): m/z 407.8 [M + H]+.

The synthetic route of 845866-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 133232-56-1, 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 133232-56-1 as follows.

3-Iodo-2-methylbenzoic acid (10.00 g, 38.16 mmol), methanol (50 ml) and concentrated sulfuric acid (0.6 ml, 11.45 mmol) were mixed, and the mixture was stirred for 5 hours while heating to reflux. The reaction solution was concentrated, ethyl acetate (80 ml) and water (30 ml) were added to the residue. The organic layer was separated and washed three times with a saturated aqueous sodium bicarbonate solution (30 ml) and once with 10% brine (30 ml) . The organic layer was concentrated, to yield the title compound (9.22 g) (yield 87.5%) .1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.67 (3H, s) , 3.90 (3H, s), 6.92 (IH, t, J = 7.8 Hz), 7.74 (IH, dd, J = 1.2 Hz, 7.8 Hz) , 7.98 (IH, dd, J = 1.2 Hz, 7.9 Hz) .

According to the analysis of related databases, 133232-56-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 773855-64-4, name is 1-Fluoro-4-iodo-2-methoxybenzene, 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 773855-64-4, name: 1-Fluoro-4-iodo-2-methoxybenzene

Dissolve 1-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (480 mg, 1. 9 mmol) in triethylamine (7 mL, 53 mmol) and add 3- chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (250 mg, 1. 8 mmol) followed by bis (triphenylphosphine) palladium (II) dichloride (51 mg, 0. 07 mmol) and copper (I) iodide (28 mg, 0. 15 mmol). Stir for 18 h at room temperature, concentrate, and purify by silica gel chromatography, eluting with 3 : 1 hexanes : ethyl acetate. Further purify on silica gel, eluting with 100% dichloromethane, to give the title compound as a white solid (450 mg, 94%). 1H NMR (300 MHz, CDC13) 6 3. 93 (s, 3H), 7. 04-7. 14 (m, 3H), 7. 79-7. 81 (m, 1H), 8. 51 (d, J = 2. 3 Hz, 1H), 8. 62 (d, J = 1. 7 Hz, 1H) ; MS (APCI) : m/z = 262 [M+H] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-4-iodo-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 914636-93-4, A common heterocyclic compound, 914636-93-4, name is 3-Fluoro-5-iodobenzaldehyde, molecular formula is C7H4FIO, 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.

3-Fluoro-5-iodobenzaldehyde, monomethyl malonate, and a catalytic amount of pyrrolidine are heated in pyridine. After cooling, the solvent is distilled off in vacuo. 2N HCl and ethyl acetate are added to the residue, and the phases are separated. The organic layer is washed with brine and dried over Na2SO4. After evaporation, the residue is purified by CC on silica gel with EtOAc/hexane. Evaporation of appropriate fractions yields the title compound.

The synthetic route of 914636-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PSYCHOGENICS, INCstatuts; CHANDRASEKHAR, Jayaraman; KOZIKOWSKI, Alan, P.; LIU, Jianhua; TUECKMANTEL, Werner; WALKER, Joel, R.; YUEN, Po-wai; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2010/45212; (2010); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 869365-97-9, 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. 869365-97-9, name is (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

{3-[4-Chloro-2-(2,6-difluoro-benzoyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester (3aa) (5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) (5.5 g, 14.5 mmol), prop-2-ynyl-carbamic acid tert-butyl ester (2.5 g, 16 mmol), PdCl2(PPh3)2 (0.6 g, 0.9 mmol) and Cu(I)I (0.2 g, 0.9 mmol) were suspended in anhydrous CH2Cl2 (50 mL) and the mixture was sparged with nitrogen for 30 min. Diethylamine (8 mL) was added and the solution was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes) to afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H).

The synthetic route of (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2005/256102; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 954815-11-3,Some common heterocyclic compound, 954815-11-3, name is 4-Iodo-2-(trifluoromethyl)benzoic acid, molecular formula is C8H4F3IO2, 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 solution of 4-iodo-2-(trifluoromethyl)benzoic acid (for a preparation see Intermediate 31 )(16.7 g, 52.8 mmol) in THF (150 ml) at ambient temperature under nitrogen was added 1.0 M borane-tetrahydrofuran complex (100 ml, 100 mmol, Aldrich) dropwise. The solution was heated to 80 0C for 1.5 h. To the solution at ambient temperature was added methanol (75 ml) and then heated to 80 0C for 1 h. The solvent was removed in vacuo to leave a mobile oil. The residue was partitioned between ethyl acetate (200 ml) and 2 N aqueous HCI (100 ml). The phases were separated and the organic phase washed with 2 N aqueous sodium hydroxide (100 ml), brine (50 ml), then dried (MgSO4), filtered and the solvent removed in vacuo to give [4-iodo-2-(trifluoromethyl)phenyl]methanol as a pale brown solid (14.8 g).

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

Reference:
Patent; GLAXO GROUP LIMITED; ALLEN, David, George; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; SOLLIS, Steven, Leslie; VILE, Sadie; WILSON, Caroline; WO2010/122089; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 172681-47-9, 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. 172681-47-9, name is 2-Amino-6-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows.

[00266] N-Acetyl-3-Iodo-2-Methyl Aniline. Charge a 5 L, 3 neck flask equipped with a mantle, stirrer, condenser, with 708 grams (5M) 3-Iodo-2-Methyl Aniline, followed by 700ml glacial acetic acid. Add in a stream of 520 grams (5.1M) acetic anhydride and allow the solution to come to a gentle reflux for an hour. The solution is allowed to cool and poured in a stream in a large container of 8L ice water. The product will crystallize immediately and is filtered and squeezed under vacuum and air-dried. Yield was 900 grams (Theoretical yield = 918 g).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-iodotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LATHAM, Keith, R.; WO2013/10102; (2013); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com