Tag: M.W=200-300

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. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6ClIO2

General procedure: A seal-tube (15 mL) initially fitted with a septum containing anilide 1 (0.5 mmol), Pd(OAc)2 (11.3 mg, 0.050 mmol, 10 mol%), and AgOAc (83.5 mg, 0.50 mmol) was evacuated and purged with N2 three times. TFA (4.0 mL) and 2-iodobenzoate 5 (0.75 mmol) were added to the system and the reaction mixture was stirred at 120 C for 24 h. The reaction mixture was cooled to r.t. and filtered through a short Celite pad and washed with CH2Cl2 several times. The filtrate was concentrated by vacuum and purified on a silica gel column using hexane/EtOAc as eluent to give the corresponding pure phenanthridone product 6.

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 181765-85-5.

Reference:
Article; Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong; Synthesis; vol. 48; 12; (2016); p. 1872 – 1879;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7, These common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, 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.

To a 50-mL round bottom flask equipped with a magnetic stir bar, a temperature probe, and a reflux condenser was charged S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amino)-3-oxopropyl) ethanethioate (1.0 g, 3 mmol, 96% HPLC purity) and MeOH (30 mL). To the suspension was added NaOMe (0.497 g, 9 0 mmol) and the reaction mixture was stirred at room temperature for 30 min, at which point HPLC analysis indicated that <0.3% of S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amino)-3-oxopropyl) ethanethioate remained. 1,1,1-Trifluoro-3-iodopropane (2.06 g, 9. 0 mmol) was added and the mixture was heated at 50 C. for 30 min, at which point HPLC analysis indicated that <1.5% of thiol intermediate remained. The reaction mixture was cooled to room temperature, filtered, and the filter cake washed with MeOH (10 mL) The filtrate was concentrated to afford crude product as an off-white solid (2.0 g, 90% HPLC purity), which was purified by flash column chromatography (0-100% EtOAc/hexanes) to afford the desired product as a white solid (1.0 g, 86%, 98.2% HPLC purity). mp 111-114 C. 1H NMR (400 MHz, CDCl3): 8.97 (s, 1H), 8.63 (s, 1H), 8.54 (d, J=4.6 Hz, 1H), 7.97 (d, J=9.4 Hz, 1H), 7.64 (s, 1H), 7.39 (dd, J=8.3, 4.8 Hz, 1H), 2.95 (t, J=6.8 Hz, 2H), 2.75 (m, 4H), 2.32-2.50 (m, 2H). 13C NMR (101 MHz, CDCl3): 168.3, 147.9, 140.1, 136.1, 132.5, 127.4, 125.9, 124.7, 124.1, 120.0, 36.5, 34.7 (q, J=29 Hz), 27.6, 24.6. ESIMS m/z 378.9 ([M+H]+). The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings. 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

Reference of 216393-67-8, 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 216393-67-8 as follows.

4~Chloro-2-fluoro-6-iodoaniline (Intermediate 30, 1.35 g, 5 mmol), pyruvic acid (1.32 g,15 mmol) and DABCO (1.68 g,15 mmol) were dissolved in DMF(15 mL). The solution was degassed and palladium acetate (56 mg) was added. The mixture was then heated to 1000C for 3h., cooled to ambient and filtered. The filtrate was diluted with EtOAc (100 mL), washed with 2M HCl (2 x 2OmL), water (20 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave the title compound as a dark solid (0.9g, 85% ). 1H NMR (400 MHz, DMSO-de) delta 7.16 (IH, t), 7.21 – 7.24 (IH, m), 7.59 (IH, d), 12.52 (IH, s), 13.27 (IH, s); MS m/z 212 (M-H)”

According to the analysis of related databases, 216393-67-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82400; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 460-37-7 as follows. COA of Formula: C3H4F3I

Example 447A 3-(2-Methoxypropyl)-5-methyl-2,4-dioxo-1-(3,3,3-trifluoropropyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidino-6-carbaldehyde (racemate) 4.33 g (13.3 mmol) of caesium carbonate were added to a solution of 2.5 g (8.86 mmol) of the compound from Ex. 442A in 18 ml of DMF, and the mixture was stirred at RT for 10 min. Then 2.98 g (13.3 mmol) of 1,1,1-trifluoro-3-iodopropane were added, and the mixture was stirred in a microwave oven (Biotage Initiator with dynamic control of irradiation power), first at 100 C. for 3 h, then at 80 C. for 3 h. After cooling to RT, about 90 ml of water were added and the product was extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated. The remaining residue was purified by MPLC (Isolera, Biotage cartridge with 340 g of silica gel, cyclohexane/ethyl acetate 90:10-10:90). The product fractions were combined, concentrated by evaporation and dried under high vacuum. 2.8 g (83% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 10.11 (s, 1H), 4.30-4.11 (m, 2H), 4.05 (dd, 1H), 3.77 (dd, 1H), 3.63 (sext, 1H), 3.22 (s, 3H), 2.91-2.72 (m, 2H), 2.79 (s, 3H), 1.07 (d, 3H). LC/MS (Method 1, ESIpos): Rt=0.94 min, m/z=379 [M+H]+.

According to the analysis of related databases, 460-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAeRTER, Michael; KOSEMUND, Dirk; DELBECK, Martina; KALTHOF, Bernd; WASNAIRE, Pierre; SUessMEIER, Frank; LUSTIG, Klemens; (369 pag.)US2018/65981; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 127654-70-0, name is 1-Chloro-3-fluoro-2-iodobenzene, molecular formula is C6H3ClFI, 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. Recommanded Product: 1-Chloro-3-fluoro-2-iodobenzene

Step 22-Chloro-6-fluoro-iodbenzene (10 g, 39 mmol) is dissolved in sulfuric acid (cone, 17 ml_) at 0 C. A mixture of nitric acid (cone, 3.2 ml_) and sulfuric acid (cone, 3.2 ml_) is added at 0 C and stirring is continued for 2 h at 25 C. The reaction mixture is pourred onto ice. The resulting precipitate is collected, dried and used without further purification for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127654-70-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STADTMUELLER, Heinz; WO2012/104388; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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. Formula: C6H3Cl2I

Method B: a mixture of 3,4-dichloroiodobenzene (300 mg), propargyl alcohol (128 muL), CuI (10 mg), K2CO3 (302 mg), Pd(PPh3)4 (12 mg) in DMF (2 mL) was irradiated with MicroWave at 100 0C for 20 min. Aqueous saturated solution NH4CI was then added followed by DCM. After separation of the two phases the organic layer was dried and evaporated in vacuo. The crude product was purified by flash chromatography (eluting with cyclohexane / ethyl acetate 7/3) to give the title compound (40 mg). NMR (1H, CDCI3): delta 7.58 (s, 1 H), 7.41 (d, 1 H), 7.27 (d, 1 H), 4.52 (d, 2H), 1.75 (t, 1 H)

The synthetic route of 1,2-Dichloro-4-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/31772; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

455-13-0, name is 4-Iodobenzotrifluoride, 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. Product Details of 455-13-0

General procedure: Step 1. To a solution of the arylhalide (1 equiv.) and propargyl alcohol (3 equiv.) in triethylamine (0.2 M) was added Pd(PPh3)4 (1 mol %) and CuI (5 mol %, dissolved in minimum necessary amount of triethylamine) under Ar. The resulting mixture was stirred at ambient temperature. After completion of the reaction, the reaction mixture was diluted with EtOAc and filtered through a short pad of SiO2 (eluent EtOAc). The filtrate was concentrated in vacuo and the crude products were purified by flash column chromatography on silica to afford the propargylic alcohol 13a – 13i.

The synthetic route of 455-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kristianslund, Renate; Aursnes, Marius; Tungen, J°rn Eivind; Hansen, Trond Vidar; Tetrahedron Letters; vol. 57; 47; (2016); p. 5232 – 5236;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7, 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. 460-37-7 name is 1,1,1-Trifluoro-3-iodopropane, 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.

: in a 100 ml dry single-mouth flask, isopropyl 2-bromo-6-methyl-5-(1-(piperazine-1-ethyl)ethyl)indolizine-7-carboxylate hydrochloride (170 mg, 0.38 mmol) was dissolved in N,N-dimethylformamide (10 mL), and 1,1,1-trifluoro-3-iodopropane (170 mg, 0.76 mmol), potassium carbonate (157 mg, 1.14 mmol) were added, the mixture was microwave-stirred at 100 C. for 2 hours, water was added, and extracted with ethyl acetate (50*3 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtrated, and solvent was removed under reduced pressure to give a yellow oil (120 mg, 63%), MS (ESI) m/z 504 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,1-Trifluoro-3-iodopropane, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI HAIHE PHARMACEUTICAL CO., LTD.; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; CHEN, Xuxing; GENG, Meiyu; JIANG, Lei; CHEN, Yi; CAO, Jianhua; JIANG, Qingyun; SHEN, Qianqian; DING, Jian; YAO, Yucai; ZHAO, Zhao; XIONG, Yuanfang; (247 pag.)US2019/211010; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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. Computed Properties of C6H3Cl2I

Palladium(II) acetate (0.17 g, 0.73 mmol) was added to a mixture of 1,2- dichloro-4-iodobenzene (2.00 g, 7.33 mmol), prop-2-en-l-ol (0.75 mL, 1 1 mmol), benzyltriethylammonium chloride (1.67 g, 7.33 mmol) and sodium bicarbonate (1.54 g, 18.3 mmol) in DMF (5 mL) and the mixture was degassed and back filled with Ar three times. The reaction mixture was heated at 60 C for 2 h. The mixture was diluted with Et20 (15 niL) and H2O (15 niL) and the mixture was filtered through a celite pad. The organic layer was separated and the aqueous layer was extracted with E20 twice. The combined organic layers were dried over MgS04, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0- 10% over 20 min, column 80 g, flow rate 40 mL/min) to give Intermediate 16A (1.0 g, 4.9 mmol, 67 % yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.78 (2 H, t, J=7.3 Hz), 2.91 (2 H, t, J=7.3 Hz), 7.03 (1 H, dd, J=8.2, 2.1 Hz), 7.29 (1 H, d, J=2.3 Hz), 7.35 (1 H, d, J=8.0 Hz), 9.81 (1 H, s).

The synthetic route of 20555-91-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/49096; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5159-41-1, name is 2-Iodobenzyl alcohol, 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. Quality Control of 2-Iodobenzyl alcohol

The reaction was carried out using o-iodobenzyl alcohol (i.e., R1 in the formula (I) o) 1.0 mmol (234.0 mg)The procedure and procedure were the same as in Example 1, aqueous ammonia (1.6 mol / L) 5.0 mL, catalyst copper sulfate was used in an amount of 5 mol% (8.0 mg)TEMPO is used in an amount of 8 mol% (12.5 mg) at a reaction temperature of 120 C and a reaction time of 18 h. The crude product is purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure title product at 206.1 mg yield of 90%.

The synthetic route of 5159-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Zhang Guofu; Zhao Yiyong; Zhang Guihua; Ding Chengrong; Yu Yidong; Lv Jinghui; (10 pag.)CN106866326; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com