Category: iodides-buliding-blocks

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,
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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

Reference of 51839-15-7, These common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, 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.

Intermediate LXII: Dimethyl-5-trifluoromethyl isophthalate; To a solution of dimethyl 5-iodoisophthalate (1 g, 3.12 mmol) in 1:1 DMF/HMPA was added Methyl- 2,2-difluoro-2( fluorosulfonyl) acetate (3 g, 15.6 mmol) and Copper (I) Iodide (2.9 mg, 15.6 mmol) and the reaction mixture heated to. 80 C for 16 h. The reaction was cooled to rt and diluted with ethyl acetate (200 mL) The solvent was decanted and the copper salts washed with an additional 100 mL of ethyl acetate. The organics were poured into water (200 mL ) the phases separated and the aqueous extracted with Ethyl acetate ( 100mL) dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane. to give dimethyl-5-trifluoromethyl isophthalate. : :¹H NMR (400 MHz, CDC13) No. 8.85 (s, 1H), 8.48 (s, 2H), 4.01 (s, 6H). LCMS [(M) +H]+ = 263.

The synthetic route of 51839-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/103020; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 159217-89-7, A common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, 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.

5 g (15,7 mmol) N-tert-Butyloxycarbonyl-4-iodanilin (BOC-geschuetztes 4-lodanilin) in 30 ml Toluol wurden bei Raumtemperatur mit einer Spatelspitze 4-Dimethylaminopyridin als Katalysator und 5,02 g (23,0 mmol) Di-tertbutyldicarbonat (BOC-Anhydrid) versetzt. Man liessueber Nacht ruehren, verduennte mit 30 ml Dichlormethan, wusch mit 20 ml 5 %iger Salzsaeure, trennte die Phasen und engte die organische Phase bis zur Trockene ein. Der Rueckstand wurde im Hochvakuum von Loesungsmittelresten befreit. Man erhielt das zweifach BOCgeschuetzte 4-lodanilin in 4,41 g (10,5 mmol, 67 %) Ausbeute. Die gesamte Menge wurde in 25 ml THF geloest und zu einer auf -78C gekuehlten Loesung von Lithiumtributylmagnesat in THF/Hexan (ca. 44 ml, 12,6 mmol) getropft (hergestellt aus Butylmagnesiumbromid-Loesung in THF und Butyllithium-Loesung in Hexan bei 0 C). Nach 40 min Nachruehren wurden 3,27 g (31,5 mmol) Trimethylborat langsam zugetropft. Man ruehrte noch 30 min bei -78C nach und liess dann langsam auf 0C erwaermen. Zur Hydrolyse wurden 70 ml 2 N methanolischer Chlorwasserstoff zugegeben und 7 h geruehrt. Zur Isolierung des Produkts gab man das Gemisch in 250 ml Wasser und 250 ml Toluol, extrahierte und trennte die Phasen. Die Toluolphase wurde eingeengt und das Produkt aus Methanol umkristallisiert. Man erhielt 0,64 g (3,7 mmol, 35 %) des 4-Anilinboronsaeure-Hydrochlorids; zusaetzlich war durch Protodeborierung eine nicht bestimmte Menge Anilin entstanden (Ausbeute ueber beide Stufen 23,5 %).

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; Clariant GmbH; EP1479686; (2004); 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

Synthetic Route of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

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

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com