Month: June 2021

Application of 766-99-4, The chemical industry reduces the impact on the environment during synthesis 766-99-4, name is 1-Ethynyl-4-iodobenzene, I believe this compound will play a more active role in future production and life.

To a suspended solution of ZnBr2 (1.10 mmol, 0.176 g) and (4-iodophenyl)ethyne (15.3 mmol, 3.50 g) in THF (40 mL) was added tributyl(methoxy)stannane (18.4 mmol, 5.91 g). The mixture was stirred for 3 h at room temperature, and then quenched by NH4F(aq) (10%, 50 mL). The obtained white precipitate was filtered off, and the filtrate was extracted with Et2O (3 x 10 mL) and dried over MgSO4. The volatiles were removed under reduced pressure to give a pure product (100% purity (A small portion was analyzed by 1H NMR using 1,1,2,2-tetrachloroethane as an internal standard to determine the purity)).

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-Ethynyl-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Suzuki, Itaru; Esumi, Naoto; Yasuda, Makoto; Baba, Akio; Chemistry Letters; vol. 44; 1; (2015); p. 38 – 40;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 31599-60-7, The chemical industry reduces the impact on the environment during synthesis 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, I believe this compound will play a more active role in future production and life.

Example AAA26 Synthesis of 4-(thiazol-2-yl)-1-(3-(2,3-dimethylphenyl)-propiolyl)piperazine 4-(Thiazol-2-yl)-1-(3-(2,3-dimethylphenyl)propiolyl)piperazine was obtained by the reaction of 4-(thiazol-2-yl)-1-propiolylpiperazine [Precursor BBB2] with 2,3-dimethyl-iodobenzene according to the conditions described in the case of Example AAA1.

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-Iodo-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; US2007/112011; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 18698-96-9,Some common heterocyclic compound, 18698-96-9, name is 2-(2-Iodophenyl)acetic acid, molecular formula is C8H7IO2, 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.

Step 1: (N,N)-Diisopropyl 2-iodophenylacetamide To a solution of 2-iodophenylacetic acid (11.0 g, 42.0 mmol, commercially available) in dichloromethane (85 mL) was added oxalyl chloride (7.11 mL, 84 mmol) followed by 2 drops of dimethyl formamide. The solution as stirred at room temperature for 2 h and the solvents were removed in vacuo. The residue was taken up in dichloromethane (100 mL) and cooled at 0° C. Diisopropylamine (17.6 mL, 126 mmol) was then added and the solution as warmed to room temperature. The solvents were removed in vacuum. The residue was partitioned between ethyl acetate and water and extracted with ethyl acetate. The combined organic layers were washed with hydrogen chloride (1N), brine, dried and concentrated to give 14.3 g of (N,N)-Diisopropyl 2-iodophenylacetamide (White solid, 99percent). C14H20INO, MW: 345.23; LCMS (method A) RT 1.90 min; Mass 346 (100percent, MH+), 268 (10percent, MNa+); IR: 2965, 1634, 1438, 1369, 1337 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.84 (d, 1H), 7.22-7.35 (m, 3H), 6.84-6.97 (m, 1H), 3.91 (m, 1H), 3.76 (s, 2H), 3.43 (m, 1H), 1.46 (d, 3H), 1.15 (d, 6H) ppm.

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; Lachia, Mathilde Denise; De Mesmaeker, Alain; Wolf, Hanno Christian; Jung, Pierre Joseph Marcel; US2013/303375; (2013); 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. 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Iodo-1,2-dimethylbenzene

14 Typical procedure for the preparation of 4,5-disubstituted-1,2,3-(NH)-triazoles (synthesis of 3a): A round-bottom sidearm flask (10 mL) containing PdCl2(PPh3)2 (0.015 mmol) was subjected to the Schlenk-line procedures of evacuation and purging of CO for three cycles. Iodobenzene and 4 equiv Et3N (1.2 mmol) were successively added, and the mixture was stirred at room temperature for 10 min, then 1-hexyne (0.45 mmol) was added, continuously stirred at room temperature for 14 h. Then NaN3 (35.1 mg, 0.54 mmol) and 1 mL DMSO were added to the mixture and the reaction continued at 45 C for 36 h. Following, to the reaction mixture was added water (2 mL), 20% HCl solution (1 mL) and extracted with ether (3 * 10 mL). The combined organic phases were washed with brine (2 * 5 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to flash column chromatography with hexanes/EtOAc (5/1) as eluent to obtain the desired 3a (56.33 mg, 82% yield). All products gave satisfactory spectroscopic and analytical data.

According to the analysis of related databases, 31599-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Na; Wang, Dong; Li, Jihui; Shi, Weilin; Li, Chao; Chen, Baohua; Tetrahedron Letters; vol. 52; 9; (2011); p. 980 – 982;,
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. 696-41-3, name is 3-Iodobenzaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 3-Iodobenzaldehyde

General procedure: In the glove box, zinc powder (206.0 mg, 3.15 mmol) was added into a Schlenk tube. Anhydrous DMF (10.5 mL) was added and the mixture was stirred at room temperature. Chlorotrimethylsilane (66.5 muL, 0.52 mmol) was then added into the mixture to activate zinc powder. Five minutes later, PhSO2CF2Br (2) (2.1 mmol) was added into the suspension. The reaction proceeded smoothly in 15 min to give (phenylsulfonyl)difluoromethylzinc reagent (?XZnCF2SO2Ph?, 3). The mixture was kept at room temperature to precipitate the remaining zinc powder, and the solution was directly used for next step. In the glove box, 2-naphthaldehyde (156.2 mg, 1.0 mmol) was added into another Schlenk tube. Anhydrous DMF (5 mL) was added and the mixture was stirred at room temperature. The DMF solution of ?XZnCF2SO2Ph? (3) (10 mL, corresponding to the reaction of ca. 2.0 mmol of PhSO2CF2Br and ca. 3.0 mmol of zinc powder) was added to the solution of 2-naphthaldehyde dropwise. The mixture was stirred at room temperature for 5 h, and aqueous HCl (2 M, 10 mL) was added to quench the reaction. After extraction with ethyl acetate for three times, the organic phase was washed with brine, and then dried over anhydrous Na2SO4. After the solution was filtered and evaporated under vacuum, the residue was subjected to silica gel column chromatography (eluting with petroleum ether/ethyl acetate) to give the corresponding difluoromethylated carbinol 4a as a white solid (307.5 mg, 88%).

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; Jiang, Fanzhou; Ni, Chuanfa; Hu, Jinbo; Journal of Fluorine Chemistry; vol. 198; (2017); p. 67 – 75;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 19099-54-8, These common heterocyclic compound, 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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.

0.3 mmol of sodium carbonate and 0.1 mmol of 1,2-bis(thiophen-2-yl)acetylene,Tetrakis(triphenylphosphine palladium) 0.005 mmol, bis(2-diphenylphosphinophenyl)ether 0.005 mmol,0.2 mmol of 4-methylbenzeneboronic acid, 0.3 mmol of 2-isopropyliodobenzene, and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography to give 31.2mg of the desired product, yield 78%.

The synthetic route of 19099-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (20 pag.)CN109879713; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 75581-11-2, A common heterocyclic compound, 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene, molecular formula is C8H9IO, 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: A DMF solution (8mL) of the o-substituted aryl iodide (0.36mmol), the o-bromobenzyl alcohol (0.36mmol) and norbornene (34mg, 0.36mmol) was added under nitrogen to a Schlenck-type flask, containing Pd(OAc)2 (4mg, 0.018mmol), the phosphine (0.036mmol), when required, and K2CO3 (124mg, 0.90mmol) or CsOPiv (211mg, 0.90). The reaction mixture was stirred at 105C for 24h. After cooling to room temperature the organic layer was diluted with EtOAc (20mL), washed twice with water (20mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using mixtures of hexane-EtOAc as eluent.

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; Della Ca, Nicola; Fontana, Marco; Xu, Di; Cremaschi, Mirko; Lucentini, Riccardo; Zhou, Zhi-Ming; Catellani, Marta; Motti, Elena; Tetrahedron; vol. 71; 37; (2015); p. 6389 – 6401;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 702641-04-1, name is 2-Iodo-5-(trifluoromethyl)benzoic acid, 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 702641-04-1, Application In Synthesis of 2-Iodo-5-(trifluoromethyl)benzoic acid

To a cooled (ice water bath) mixture of 2-iodo-5-(trifluoromethyl)benzoic acid (2.5 g, 7.9 mmol) in tetrahydrofuran (50 mL) and methanol (10 mL) was added dropwise a 0.6 M solution of trimethylsilyldiazomethane in hexane (TCI America, 16 mL, 9.9 mmol) via syringe. After LC/MS analysis confirmed the consumption of the starting acid, acetic acid (approximately 3 mL) was added. The mixture was concentrated under reduced pressure, and the putative desired intermediate was carried forward without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-5-(trifluoromethyl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; Farand, Julie; Kaplan, Joshua A.; Notte, Gregory; Olen, Casey Lockwood; Sangi, Michael; Sperandio, David; (115 pag.)US2019/359565; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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. Application In Synthesis of 1,1,1-Trifluoro-3-iodopropane

A vial was charged with activated zinc (Rieke Zinc) (4.38 ml, 3.35 mmol) and cooled to 0C. 1,1,1-trifluoro-3-iodopropane (0.268 ml, 2.233 mmol) was added slowly dropwise and the reaction was warmed to room temperature and stirred for one hour. Palladium(II) acetate (2.73 mg, 0.012 mmol), 2?-(dicyclohexylphosphino)-N2,N2,N6,N6- tetramethyl-[ 1,1 ?-biphenylj -2,6-diamine (CPhos) (10.60 mg, 0.024 mmol), and 1 -(4-bromo-5- fluoro-2-methoxyphenyl)-N-(isoxazol-3 -yl)-2-oxo- 1 ,2-dihydroquinoline-6-sulfonamide (See above Intermediate B 1, 0.100 g, 0.202 mmol) were added and the reaction was stirred for two hours at 50 C. The reaction was diluted with ethyl acetate and washed twice with iN HC1 solution. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40g, gradient elution 0-100% EtOAc :Heptane) to afford (P)- 1 -(5 -fluoro-2-methoxy-4-(3 ,3,3 – trifluoropropyl)phenyl)-N-(isoxazol-3 -yl)-2-oxo- 1 ,2-dihydroquinoline-6-sulfonamide (0.067 g, 0.131 mmol, 64.8 % yield) as a white solid. 1H NMR (400 MHz, DM50-cl6) oe = 2.64 – 2.78 (m, 2 H) 2.87-3.03 (m, 2 H) 3.66 (s, 3 H) 6.44 (d, J1.81 Hz, 1 H) 6.77 (dd, J15.32,9.30 Hz, 2 H) 7.30 – 7.41 (m, 2 H) 7.84 (dd, J=8.97, 2.23 Hz, 1 H) 8.21 (d, J=9.69 Hz, 1 H)8.36 (d, J=2.18 Hz, 1 H) 8.73 (d, J=1.76 Hz, 1 H) 11.65 (s, 1 H). m/z (ESI) 512.2 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 460-37-7, its application will become more common.

Reference:
Patent; AMGEN INC.; WEISS, Matthew; MILGRAM, Benjamin C; MARX, Isaac E.; DINEEN, Thomas; (63 pag.)WO2017/106871; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 10297-05-9, These common heterocyclic compound, 10297-05-9, name is 1-Chloro-4-iodobutane, 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 1503-(2-isopropylphenyl)-5-(4-morpholin-4-ylbutoxy)-l -(3-( 1 -naphthyloxy)propyl)- 1 H-indole-2-carboxylic acidA mixture of EXAMPLE 149A (36 mg), l-chloro-4-iodobutane (0.043 ml) and cesium carbonate (116 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature overnight. The inorganic salt was filtered off. To the N,N-dimethylformamide solution was added morpholine (0.2 ml) and the resulting mixture was heated at 600C for 5 hours. The reaction mixture was concentrated and the residue was purified by RPHPLC (mobile phase: 10percent-100percent acetonitrile in 0.1percent TFA aqueous solution during 60 min) on a C18 column to give ethyl 3-(2-isopropylphenyl)-5-(4-morpholinobutoxy)-l-(3-(naphthalen- l-yloxy)propyl)-lH-indole-2-carboxylate. This ester was hydrolyzed with aqueous NaOH in a mixture of tetrahydrofuran and methanol to provide the title compound. 1H NMR (400 MHz, dimethyl sulfoxide-d6) ? 9.52 (s, IH), 8.20 (d, J=8.29Hz, IH), 7.87 (d, J=7.98Hz, IH), 7.59 (d, J=8.90Hz, IH), 7.43-7.57 (m, 3H), 7.30-7.43 (m, 3H), 7.14-7.23 (m, IH), 7.06 (d, J=7.36Hz, IH), 6.89 (dd, J=9.05, 2.30Hz, IH), 6.85 (d, J=7.67Hz, IH), 6.43 (d, J=2.45Hz, IH), 4.88 (t, J=7.21Hz, 2H), 4.15 (t, J=5.83Hz, 2H), 3.89-4.03 (m, J=I 1.97Hz, 2H), 3.75-3.89 (m, 2H), 3.55-3.70 (m, 2H), 3.07-3.17 (m, 2H), 3.02 (s, br, 2H), 2.61-2.78 (m, 2H), 2.23-2.45 (m, 2H), 1.60-1.85 (m, 4H).

The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/130970; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com