Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), 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 627-31-6, Computed Properties of C3H6I2

To a solution of ethyl 2-(4-nitrophenyl)acetate (9.0 g, 43 mmol) in DMF (100 mL) was added NaH (3.6 g, 90 mmol, 60% in oil) at 0 C. Then the reaction mixture was allowed to warm to RT and stirred for 15 min. The mixture was cooled to 0 C again and 1,3- diiodopropane (10 mL, 89 mmol) was added. The resulting mixture was stirred at 0 C for 30 min, then warmed to RT and stirred at RT for 1 h. The reaction was diluted with NH4C1 (sat., 200 mL), extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (EtOAc in petroleum ether: 0 – 5% gradient) to give the title compound (I-D). lH NMR (400 MHz, CDC13) delta 8.23 – 8.12 (m, 2 H), 7.52 – 7.38 (m, 2 H), 4.18 – 4.04 (m, 2 H), 2.94 – 2.82 (m, 2 H), 2.57 – 2.45 (m, 2 H), 2.18- 2.04(m, 1 H), 2.00- 1.75 (m, 1H), 1.22 – 1.12 (m, 3 H).

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; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 461-17-6, 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 461-17-6 as follows.

Example 2; 1-(2,4-Dichlorophenyl)-4-methyl-5-[4-(4,4,4-trifluorobutoxy)-phenyl]-1H-pyrazole-3- carboxylic acid piperidin-1-ylamide; 1- (2, 4-Dichlorophenyl)-5- (4-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-l-yl amide from Ex 1, Step F (250 mg, 0.56 mmol) was dissolved in acetone (10 ml) and potassium carbonate (77 mg, 0.56 mmol) was added followed by 1-iodo-4, 4,4- trifluorobutane (140 mg, 0.56 mmol). The reaction mixture was boiled under reflux overnight, concentrated and purified by flash chromatography (hexane : EtOAc 70: 30- 60: 40) afforded 130 mg (42%) of a white solid that was triturated with hexane: EtOAc 95 : 5 and filtered. ‘H NMR (CDC13) : 5 7.63 (1H, broad s), 7.43 (1H, m), 7.30 (2H, m), 7.10-7. 00 (2H, m), 6.85-6. 78 (2H, m), 4.05 (2H, t), 2.90 (4H, m), 2.40-2. 19 (SH, s and m), 2.15-1. 97 (2H, m), 1. 78 (4H, m), 1.45 (2 H, m) MS m/z 577 (M+Na). HPLC: 98.4%

According to the analysis of related databases, 461-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/80343; (2005); A2;,
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. 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-iodo-2-methylbenzoate

0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.0.02 mmol of triphenylphosphine, 0.2 mmol of methyl 2,3-dicarboxylate-7-oxanorbornadiene,2-fluoro-3-carboxylic acid methyl ester iodobenzene 0.1 mmol, hexamethyldisiloxane 0.15 mmol,1 mL of N,N-dimethylformamide was added to a 15 mL reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography19.2mg of target product,The yield was 60%.

According to the analysis of related databases, 52570-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (13 pag.)CN109021003; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 61272-76-2, A common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, molecular formula is C6H5FIN, 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 64 4-(((2-tert-Butyl-5-fluoro-1H-indol-3-yl)methoxy)methyl)-N,N-dimethyl-1-phenylcyclohexanamine (one of two possible diastereomers) A mixture of Ain-13 (522 mg, 1.60 mmol), 4-fluoro-2-iodoaniline (Ian-04) (453 mg, 1.90 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-3-chloropyridyl palladium(II) chloride (PEPPSI, 109 mg, 0.16 mmol) and sodium carbonate (848 mg, 8.0 mmol) was evacuated for 30 min (oil pump). The mixture was then flushed with argon and absolute N,N-dimethyl formamide (5 ml, previously flushed for 1 h with argon) was added with a syringe via a Schlenk attachment. The reaction mixture was stirred for 18 h at 10° C., during the course of which the solution turned a dark brown colour. The reaction solution was then concentrated to small volume under vacuum, the residue was taken up repeatedly in toluene (3*30 ml) and concentrated to small volume again each time, then divided between water and ethyl acetate (50 ml each) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2*50 ml), the combined organic phases were washed with 1 M sodium thiosulfate solution and saturated sodium chloride solution (50 ml each), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (948 mg) was purified by flash chromatography (38 g, 20*2.5 cm) with chloroform/methanol (1:5). Yield: 421 mg (60percent) Melting point: 51-53° C. 1H-NMR (DMSO-d6): 1.19-1.68 (m, 7H); 1.44 (s, 9H); 1.89 (s, 6H); 2.54-2.64 (m, 2H); 3.29-3.31 (m, 2H); 4.64 (s, 2H); 6.84 (dt, 1H, J=2.5, 9.6 Hz); 7.23 (dd, 2H, J=2.5, 10.2 Hz); 7.27 (d, 1H, J=4.7 Hz); 7.29-7.37 (m, 4H); 10.79 (s, 1H). 13C-NMR (DMSO-d6): 24.5; 30.3; 32.1; 33.2; 37.0; 37.4; 58.5; 63.2; 74.5; 102.2 (d, 1C, J=23 Hz); 106.6; 108.1 (d, 1C, J=26 Hz); 111.6 (d, 1C, J=0 Hz); 126.1; 126.5; 127.2; 129.8 (d, 1C, J=10 Hz); 130.7; 139.4; 147.5; 156.9 (d, 1C, J=231 Hz). Other C signals were unable to be identified.

The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 181765-86-6, 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. 181765-86-6 name is Methyl 5-bromo-2-iodobenzoate, 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.

A mixture of 1 ,4-benzenediboronic acid bis(pinacol) ester (4.40 g, 13.33 mmol), methyl 2-iodo-5-bromobenzoate (9.95 g, 29.18 mmol), and Aliquat 336 (1.60 mL) was degassed 3 times with N2 before 90.0 mL of dry toluene was added. Tetrakis(triphenylphosphine)palladium (1.50 g, 1.30 mmol) and IM aqueous sodium carbonate solution (5.73 g in 54.0 mL of water) which was already deaerated for 2 hours were added under N2. The mixture was stirred vigorously and heated at the refluxing temperature for 2 days and allowed to cool to room temperature. The solution was passed through a plug of Celite to remove palladium black and the filtrate was concentrated to provide a residue, which was purified by column chromatography (silica gel, chloroform) to afford 4,4″-dibromo-2,2″- methoxycarbonyl-[l,l’;4′,l “]terphenyl (17) as a white solid (6.00 g, 89% yield). 1H NMR (CDCl3): delta 3.72 (s, 6H), 7.32(d, 2H, J = 8.0 Hz), 7.33 (s, 4H), 7.69(d, 2H, J = 8.0 Hz), 8.01 (s, 2H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-bromo-2-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2009/17798; (2009); A1;,
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. 41252-98-6, name is 1-Iodo-2-methyl-3-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6INO2

4.1.11. 2,20-Dimethyl-3,30-dinitro-1,10-biphenyl (27)4.1.11.1. Activation of copper powder:.34 Copper powder (2.00 g)was stirred with 2% iodine (w/w wrt copper) in acetone (100 mL)for 10 min. The powder was filtered and stirred to form a slurrywith 1:1 solution of concentrated hydrochloric acid in acetone(200 mL). The copper iodide dissolved, and the copper powderremaining was removed by filtration and washed with acetone(200 mL). The activated copper was dried in a vacuum desiccatorand used immediately.2-Methyl-3-nitro-iodobenzene (26) (1.00 g, 3.80 mmol) andactivated copper (1.21 g, 19.0 mmol) were added to dry N,Ndimethylformamide(8 mL), and the mixture was heated to 190 Cfor 24 h. The mixture was diluted with dichloromethane (100 mL),washed with 4% aqueous ammonia (5100 mL), water (450 mL),and brine (350 mL), dried (Na2SO4), and the solvents removedunder reduced pressure to yield a dark crude oil. Column chromatographyof the residue using ethyl acetate/petroleum ether(1:10) gave the product as a yellow solid (0.27 g, 53%); mp120e121 C; nmax (film)/cm1 3086, 1604, 1524, 1458, 1350, 1279,1219, 1106, 995, 859, 807, 736, 718, 674; 1H NMR (400 MHz, CDCl3):d 2.13 (6H, s, 2 CH3), 7.29 (2H, dd, J7.6, 1.4 Hz, 2 CH arom., biphenyl-5,50), 7.36 (2H, ddd, J8.0, 7.6, 0.5 Hz, 2 CH arom., biphenyl-6,60), 7.83 (2H, dd, J8.0, 1.4 Hz, 2 CH arom., biphenyl-4,40); 13CNMR (100 MHz, CDCl3): d 15.4 (2 CH3, 2 ArCH3), 123.1 (2 CHarom., biphenyl-4,40),125.7 (2 CH arom., biphenyl-5,50),129.8 (2 Cquat., arom., biphenyl-2,20), 132.6 (2 CH arom., biphenyl-6,60), 141.3(2 C quat., arom., biphenyl-1,10), 149.9 (2 C quat., arom., biphenyl-3,30); m/z (EI) 272.0793; C14H12N2O4 (M) requires 272.0797.

According to the analysis of related databases, 41252-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Farah, Mohamed M.; Page, Philip C. Bulman; Buckley, Benjamin R.; Blacker, A. John; Elsegood, Mark R.J.; Tetrahedron; vol. 69; 2; (2013); p. 758 – 769;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 450412-29-0, 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. 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

200 g (664 mmol) of 1-bromo-3-fluoro-2-iodobenzene,101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate were dissolved in 1000 ml of THF and 600 ml of water and degassed.9.3 g (13.3 mmol) of bis (triphenylphosphine) palladium (II) dichloride and 1 g (20 mmol) of hydrazine hydroxide were added.The reaction mixture was stirred at 70 C for 48 hours under a protective atmosphere.Toluene was added to the cooled solution,Wash repeatedly with water, dry and concentrate.The product was purified by silica gel column chromatography with toluene / heptane (1: 2). Yield: 155 g (553 mmol),Theoretical yield 83%.

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, 1-Bromo-3-fluoro-2-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; PARHAM, AMIR HOSSAIN; LUDEMANN, AURELIE; JOOSTEN, DOMINIK; GROSSMANN, TOBIAS; KROEBER, JONAS VALENTIN; (90 pag.)TW2017/31839; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7, 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.

To a solution of N-isopropylpropan-2-amine (9.45 g, 93.35 mmol, 13.2 mL, 2 eq) in THF (100 mL) at -40 C. was added dropwise n-BuLi (2.5 M in hexanes, 28 mL, 1.5 eq) and the mixture was stirred at -10 C. for 1 h, then cooled to -70 C. A solution of ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (10 g, 46.67 mmol, 1 eq) in THF (50 mL) was added dropwise and the reaction mixture was stirred at -70 C. for 1 h. A solution of 1,1,1-trifluoro-3-iodo-propane (15.68 g, 70.0 mmol, 8.21 mL, 1.5 eq) in THF (50 mL) was then added dropwise at -70 C. and the mixture was stirred for 14 hr at RT. The reaction was quenched by addition of saturated aq. NH4Cl (200 mL) and extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine (200 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (PE to PE: EtOAc=50:1) to give the title compound (10 g, 32.2 mmol, 69% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): delta 4.20-4.15 (m, 2H), 3.93 (s, 4H), 2.18-2.13 (m, 2H), 2.03-1.96 (m, 2H), 1.78-1.73 (m, 2H), 1.67-1.66 (m, 2H), 1.60-1.57 (m, 2H), 1.54-1.48 (m, 2H), 1.28-1.25 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 1,1,1-Trifluoro-3-iodopropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; MCAFOOS, Timothy Joseph; (166 pag.)US2019/270739; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 25309-64-2,Some common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, molecular formula is C8H9I, 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: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

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

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature 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: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.1mg, 0.05mmol), iodobenzene (1) (or an other iodoaromatics, 2-18) (1.0mmol), and 2-amino-1,3,4-thiadiazol (a) (or its 5-substituted derivatives, b or c, or 2-amino-1,3-thiazole, d) (121.4mg, 1.2mmol) and triethylamine (0.5mL) were dissolved in DMF (10mL) under argon in a 100mL three-necked flask equipped with reflux condenser connected to a balloon filled with argon. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 70C and analyzed by TLC and GC-MS. The cooled reaction mixture was then concentrated and evaporated to dryness under reduced pressure. (0025) Method A. (2a, 14a, 1d-8d, 10d, 14d-16d): The residue was dissolved in chloroform (15mL) and washed three times with water (30mL). The organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure to a solid material. Aforesaid compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm), EtOAc/CHCl3 eluent mixtures (the exact ratios are specified in Characterization for each compound; isolated yields are not optimized). (0026) Method B. (1a, 3a-13a, 15a-17a, 1b, 2b, 13b, 1c, 2c, 9d, 11d-13d, 17d): Toluene (15mL) was added to the residue, the insoluble material (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gergely, Mate; Kollar, Laszlo; Tetrahedron; vol. 74; 16; (2018); p. 2030 – 2040;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com