Tag: M.W=200-300

Synthetic Route of 31599-61-8, These common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, 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: To a stirred solution of Pd cNPs/C Fe3O4 (20 mg, 0.73 mol %) and DMF (3 mL) in a Schlenk tube with a teflon stopcock, iodobenzene (0.5 mmol), tri-n-butylphenylstanane (0.6 mmol) and K2CO3 (1.5 mmol) are added, sealed and heated at 100 oC for 10 h. After completion of the reaction, the catalyst is separated by an external magnet. After removal of catalyst, water was added to the solution and extracted with ethylacetate. The organic phase is dried over anhydrous Na2SO4. After evaporation of the solvents, the residue is subjected to column chromatography over silica gel (60-120 mesh), eluting with pet ether to afford the desired product. The biphenyl products were confirmed by 1H and 13C-NMR. The spectral data and spectra are shown in supporting information (Figure S5-S18). This procedure was followed for all the reactions listed in Table 2.

The synthetic route of 31599-61-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Basuvaraj Suresh; Anbarasan, Rajagopal; Amali, Arlin Jose; Pitchumani, Kasi; Tetrahedron Letters; vol. 58; 33; (2017); p. 3276 – 3282;,
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. 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Iodo-4-(trifluoromethoxy)benzene

Example 15 Preparation of 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C7) 3-(4-Bromophenyl)-1H-1,2,4-triazole (C6) (10.9 g, 48.5 mmol), copper(I) iodide (2.38 g, 12.5 mmol), and cesium carbonate (30.3 g, 93.0 mmol) in a round-bottomed flask was flushed with nitrogen. Dimethylsulfoxide (85 mL) was added, followed by 1-iodo-4-(trifluoromethoxy)benzene (13.2 g, 45.8 mmol). The reaction was degassed for 5 minutes, then heated at 100° C. for 3 days. The reaction was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of Celite® rinsing with ethyl acetate. To the filtrate was added saturated ammonium chloride and stirred for 1.5 hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3*). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite®. Purification by flash column chromatography using 0-40percent EtOAc/hexanes as eluent provided the title compound as an off-white solid (9.65 g, 52percent): mp 109-112° C.; 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H), 8.10-8.03 (m, 2H), 7.83-7.75 (m, 2H), 7.64-7.57 (m, 2H), 7.42-7.35 (m, 2H); ESIMS m/z 386 ([M+2H]+).

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; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Goldsmith, Miriam E.; (77 pag.)US2016/24026; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, 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 (4-Iodophenyl)methanamine hydrochloride

A mixture of (4-iodophenyl)methanamine hydrochloride (5.0 g, 18.55 mmol, 1.0 eq), (lS,2S)- Nl,N2- dimethylcyclohexane-l, 2-diamine (0.59 mL 3.71 mmol, 0.2 eq), Sodium ascorbate (368 mg, 1.86 mmol, 0.1 eq), Copper Iodide (530 mg, 2.78 mmol, 0.15 eq), Sodium azide (2.41 g, 37.1 mmol, 2.0 eq) , Et3N (3.11 mL, 22.26 mmol, 1.2 eq) and 2-(prop-2-yn-l-yloxy)tetrahydro- 2//-pyran (2.6 g, 18.55 mmol, 1.0 eq) in Methanol (50 mL) and water (12 mL) were purged with Nitrogen for 5 minutes and heated to 55 C for over night. The reaction mixture was cooled to room temperature and filtered through 413 filter paper. Celite was added and the solvent was removed under reduced pressure and the residue was purified over silica gel (120 g) using dichloromethane/(methanol containing 12 % (v/v) aqueous ammonium hydroxide) as mobile phase. The concentration of (methanol containing 12 % (v/v) aqueous ammonium hydroxide) was gradually increased from 0 % to 6.25 % to afford (4-(4-(((tctrahydro-2//-pyran-2- yl)oxy)mcthyl)- 1 H- 1 ,2,3-triazol- 1 -yl)phcnyl)mcthanaminc (15, 3.54 g, 66%) as a white solid. LCMS m/z: [M + H]+ Calcd for CI5H20N4O2 289.2; Found 289.2.

The synthetic route of 59528-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; MILLER, Robert, James; BARNEY, Lauren, Emily; JOHNSTON, Erika, Ellen; HEIDEBRECHT, Richard; BEAUREGARD, Michael; VEISEH, Omid; CARMONA, Guillaume; GONZALEZ, Francisco, Caballero; OBERLI, Matthias, Alexander; PERITT, David; SMITH, Devyn, Mckinley; WOTTON, Paul, Kevin; O’CONNOR, Owen; SEWELL, Jared, A.; (204 pag.)WO2019/195055; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 58755-70-7, 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 58755-70-7 as follows.

Intermediate 5: (“2£r)-3-(4-Methoxgamma-2-nitrophenyl’)acrylate A solution of 4-iodo-3-nitroanisole (10 g, 36 mmol), methylacrylate (3.87 mL, 43 mmol), tris(4-methylphenyl)phosphine (1.1 g, 3.6 mmol) and triethylamine (6.05 mL, 43 mmol) was degassed and flushed with nitrogen. Palladium(II) acetate (1.2 g, 1.8 mmol) was added and the mixture was heated at 7O0C overnight. It was filtered through a 0.45 mum membrane and the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate (300 mL), it was washed with potassium phosphate buffer (IM, pH 7, 2x 300 mL) and dried over sodium sulfate. Chromatography on silica gel with dichloromethane, followed by precipitation from dichloromethane (50 mL) with hexanes (500 mL) gave 4.96 g (58% yield) of product as a yellow solid.MS (ES): 260.20 (MNa+) for CnHnNO51H-NMR (DMSO-cUi delta: 3.73 (s, 3H); 3.88 (s, 3H); 6.59 (d, IH); 7.33 (dd, IH); 7.57 (d, IH); 7.78 (d, IH); 7.94 (d, IH).

According to the analysis of related databases, 58755-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/134378; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, 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 51628-12-7, name: 2-(4-Iodophenyl)acetonitrile

Preparation 10 4-(4-Iodophenyl)-tetrahydropyrane-4-carbonitrile. To a solution of (4-iodophenyl)-acetonitrile (2.43 g, 10.0 mmol) in DMSO (50 ml) was added sodium hydride (60% in oil, 1.2 g, 30 mmol) at room temperature. After stirring for 30 min., bis-2-chloroethyl ether (1.57 g, 11 mmol) was added. After stirring for a further 1 hr. at room temperature, the solution was poured into brine/water (1:1) and extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography (15% ethyl acetate in petroleum ether), giving the title compound as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Iodophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; LEO PHARMA A/S; US2012/101039; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 33348-34-4, 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. 33348-34-4, name is 4-Amino-3-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a flame-dried flask, AlMe3 (2 M in toluene, 1.11 mL, 2.18mmol, 1.2 equiv) was added to dry toluene (3.0 mL) under anitrogen atmosphere. The mixture was cooled to 0 C, and the2-iodoaniline (2.0 mmol, 1.1 equiv) in dry toluene (4.0 mL) was added. The mixture was stirred for a further 5 min at 0 C. Theice bath was removed, and the mixture was stirred for 20 min atroom temperature. The mixture was cooled to 0 C again, and cyclopentene carboxylate 2b (1.82 mmol, 1.0 equiv) in drytoluene (3.0 mL) was added dropwise over 2 min to the mixture. After stirring for 10 min at 0 C, the mixture was heated to 60 C, and stirring was continued for 16 h. After cooling to room temperature, HCl (1 M, 8.0 mL) was added. (Caution: gas evolution,exotherm.) The mixture was stirred for 15 min, then water (20 mL) and EtOAc (30 mL) were added. The mixture was extracted, the organic phase was separated, and the aqueous phase was re-extracted one more time with EtOAc (30 mL). Thecombined organic phases were washed with brine and dried (MgSO4). After filtration, the solvent was removed under reduced pressure, and the crude mixture was purified by column chromatography.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-iodobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Adeyemi, Ahmed; Wetzel, Alexander; Bergman, Joakim; Branalt, Jonas; Larhed, Mats; Synlett; vol. 30; 1; (2019); p. 82 – 88;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 135050-44-1, 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. 135050-44-1, name is 3-Chloro-4-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-chloro-4-iodobenzenamine (500 mg, 1.97 mmol), 4- chlorophenylboronic acid (324 mg, 2.07 mmol), Na2CO3 (627 mg, 5.92 mmol) andPd(PPh3)4 (228 mg, 0.20 mmol) in 1,4-dioxane (21 mL) and H20 (4 mL) was stirred at80 C under argon for 16 h. The mixture was allowed to cool to RT and concentrated invacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate / petroleum ether = 5/1) to afford the desired product (424 mg, 91% yield) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-4-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARAXES PHARMA LLC; JANES, Matthew, Robert; PATRICELLI, Matthew, Peter; LI, Liansheng; REN, Pingda; LIU, Yi; (397 pag.)WO2016/44772; (2016); A1;,
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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, A new synthetic method of this compound is introduced below., name: 2-Chloro-4-fluoro-1-iodobenzene

Step I: 2-Chloro-4-fluoroiodobenzene (9.03g, 35.22mmol, 2.00eq), potassium hydroxide solution (4M, 22.01mL,5.00eq) and bis(triphenylphosphine)palladium dichloride (617.94mg, 880.50umol, 0.05eq) were added to a solution of11 (8.30g, 17.61mmol, 1.00eq) in 100mL dimethyltetrahydrofuran. The reaction solution was stirred at 70C undernitrogen atmosphere for 12 hours, then filtered through celite, and the filtrate was washed twice with 100mL brine. Theorganic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product, which waspurified by silica gel column chromatography (PE:EA=40:1-10:1) to give the product 13 as a yellow solid (4.50g, 5.57mmol,yield 31.65%, purity 58.7%). MS [ESI, M+1]: 474.3.

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; Luoxin Biotechnology (Shanghai) Co., Ltd.; Shandong Luoxin Pharmaceutical Group Stock Co., Ltd.; LU, Jianyu; DING, Charles Z.; HU, Lihong; HE, Huijun; CHEN, Shuhui; DONG, Jiaqiang; WANG, Tie-lin; (124 pag.)EP3434668; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19230-28-5, These common heterocyclic compound, 19230-28-5, name is 1,3-Dichloro-2-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.

To toluene 3.0mL solution of tert-butyl 2-amino-4-phenethylbenzoate 0.10g were added 1,3-dichloro-2-iodobenzene 0.23g, cesium carbonate 0.22g, tris(dibenzylideneacetone)dipalladium(0) 3.0mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8.0mg at room temperature, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, palladium acetate 1.5mg, tris(dibenzylideneacetone)dipalladium(0) 3.0mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8.0mg were added, and it was stirred at 110C for 20 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 2-(2,6-dichloroanilino)-4-phenethylbenzoate. Trifluoroacetic acid 10mL was added to the obtained tert-butyl 2-(2,6-dichloroanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 75-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(2,6-dichloroanilino)-4-phenethylbenzoic acid 9.4mg of white solid. 1H-NMR(DMSO-d6) delta value: 2.76(4H,m),6.04(1H,d,J=1.2Hz),6.66(1H,dd,J=8.1,1.2Hz),7 .08-7.24(5H,m),7.36(1H,t,J=8.2Hz),7.61(2H,d,J=8.3Hz),7.80(1 H,d,J=8.0Hz),9.52(1H,s),13.00(1H,s).

The synthetic route of 19230-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 461-17-6,Some common heterocyclic compound, 461-17-6, name is 1,1,1-Trifluoro-4-iodobutane, molecular formula is C4H6F3I, 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.

Reference Example 69 fluoro-4-(4,4,4-trifluorobutoxy)benzoic acid By operating in the same manner as in Reference Example 68 and using 1,1,1-trifluoro-4-iodobutane, the title compound was obtained as colorless powder.1H-NMR (DMSO-d6) delta: 1.97 (2H, m), 2. 44 (2H, m), 4.13 (2H, t, J=6.3Hz), 6.89 (1H, t, J=2.0Hz), 6.90 (1H, m) 7.84 (1H, t, J=9.0Hz), 14.44 (1H, s).

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1447402; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com