Author: Jessica.F

612-55-5,Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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.

In an open vial with pressure-release top, a stirred mixture of 2- iodonaphthylene (Aldrich, St. Louis, MO) (64 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and ira/i5,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred for 6 hours. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtOAc (20 mL), filtered through Celite and the filter cake washed with EtOAc (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (2 prep TLC plates used) using EtOAc / hexane (1:99) as eluent to give the product (46.2 mg, 78%) as a solid.[00215] Data identical to above in Example 5.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

672-57-1, 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. 672-57-1, name is 1-Chloro-2-iodo-4-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 5:- Preparation of 7-(2-chloro-5-trifluoromethyl-phenylethynyl)-2-(2,6-dibromo- phenyl)-4,4-dimethyl-l,4-dihydro-chromeno[3,4-d]imidazole:-The mixture of 2-(2,6-dibromo-phenyl)-7-ethynyl-4,4-dimethyl-l,4-dihydro- chromeno[3,4-d]imidazole (0.500 g, 109 mol), dichloro bis (triphenyl phosphine)palladium (II) (0.022 g, 0.0327 mol), tetra butyl ammonium fluoride (0.855 g, 3.27 mol) and l-chloro-2-iodo-4-trifluoromethyl-benzene (0.501 g, 1.63 mol) was heated at 80-90C for 2-3 hours. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford desired product (0.230 g). ‘HNMR (DMSO- 6): delta 1.65 (s, 6H), 7.09-7.11 (m, 1H), 7.21-7.24 (m, 1H), 7.38-7.44 (m, 1H), 7.52 (m, 1H), 7.77-7.87 (m, 4H), 8.08 (s, 1H), 13.09 (s, 1H).

The synthetic route of 1-Chloro-2-iodo-4-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; GAJERA, Jitendra Maganbhai; NARAYANA, Lakshminarayana; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2012/110860; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

51628-12-7, 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. 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, A new synthetic method of this compound is introduced below.

General procedure: A stirred mixture of 4-iodophenylacetonitrile (35), arylboronic acid (36-45) (1.1 equiv), Pd(PPh3)4 (0.03 equiv), KBr (1.1 equiv), and K3PO4 (2.5 equiv) in dioxane (5 mL/mmol) was purged with N2 for10 min at room temperature and then stirred overnight at 85 C under N2. The mixture was diluted with water and extracted with AcOEt. The organic phase was washed three times with water, dried (Na2SO4), and evaporated under vacuum. The residue was chromatographedon silica gel.

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; Ortar, Giorgio; Morera, Enrico; De Petrocellis, Luciano; Ligresti, Alessia; Schiano Moriello, Aniello; Morera, Ludovica; Nalli, Marianna; Ragno, Rino; Pirolli, Adele; Di Marzo, Vincenzo; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 118 – 132;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 20776-55-0, name is 2-Amino-3-iodobenzoic acid, I believe this compound will play a more active role in future production and life. 20776-55-0

General procedure: A suspention of anthranilic acid A1-A17 (0.001mol), a catalytic amount of triethylamine and 4-isothiocyanato-benzenesulfonamide B17b (0.169g, 0.001mol) in absolute ethanol (25ml) was refluxed for 3. The reaction mixture was filtered while hot, left to cool and the solvent was removed under reduced pressure. The obtained residue was triturated from diethyl ether, filtered and dried under vacuo to obtain titled compound C: 1-17 as a whitish solid.

The chemical industry reduces the impact on the environment during synthesis 20776-55-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Alafeefy, Ahmed M.; Carta, Fabrizio; Ceruso, Mariangela; Supuran, Claudiu T.; Al-Tamimi, Abdul-Malek S.; Al-Kahtani, Abdulla A.; Bioorganic and medicinal chemistry; vol. 24; 6; (2016); p. 1402 – 1407;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 19099-54-8

0.3 mmol of sodium carbonate and 0.1 mmol of 1,2-bis(4-methoxyphenyl)acetylene,Tetrakis(triphenylphosphine palladium) 0.005 mmol, bis(2-diphenylphosphinophenyl)ether 0.005 mmol,0.2 mmol of [1,1′-biphenyl]-4-ylboronic 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 30.6mg of the desired product in 60% yield.

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 19099-54-8.

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

103962-05-6, 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. 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of (1S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-(4-trifluoromethoxy- phenylethynyl)-benzamide (5). Resin (3) (120 mg, 0.084 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 4-(trifiuoromethoxy)iodobenzene (4) (96.8 mg, 0.336 mmol) and Et3N (150 muL, 1.10 mmol) in DMF (2.0 mL) was purged with a stream of N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3 )2 (18.0 mg, 0.025 mmol) and CuI (8.0 mg, 0.042 mmol) were added and the mixture shaken for 24 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mL) and cleaved with 10percent TFA/DCM (2.0 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10percent TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (3.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-55percent, 0.1percent TFA, UV analysis 300 nm, 28 min) and lyophilization of the collected fractions afforded 9.0 mg (25percent yield) of (5) as a white solid. LRMS (ES+) m/z 408.0 (C19Hi6F3N3O4+H requires 408.11); RP-HPLC (300 nm, 28 min run) 18.0 min.

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; ACHAOGEN, INC.; WO2008/154642; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6828-35-9, 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. 6828-35-9, name is 5-Chloro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 5-chloro-2-iodoaniline (18.7 g, 0.074 mol, 1.0 eq.) in 500 mL of water was added hydroxylamine hydrochloride (18.5 g, 0.27 mol, 3.6 eq.), sodium sulfate (84.0 g, 0.59 mol, 8.0 eq.), chloral hydrate (14.7 g, 0.89 mol, 1.2 eq.) and 2N aqueous hydrochloric acid (25 mL). The mixture was stirred at 70 C for 18 h, then allowed to cool to room temperature. The resulting mixture was extracted with EtOAc (400 mL X 3) and the combined organic layers were dried (Na2S04), filtered and concentrated to afford compound 2 (17.0 g, 72.1% yield).

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; LUDWIG INSTITUTE FOR CANCER RESEARCH LTD; GAHMAN, Timothy; SHIAU, Andrew; KOLODNER, Richard; (234 pag.)WO2017/51251; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20776-54-9, Name is 2-Amino-4-iodobenzoic acid, 20776-54-9, 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.

[00313] Step A: To a solution of 2-amino-4-iodobenzoic acid (2.5 g, 9.50 mmol) in DMF (10 mL) at rt under argon were added EDCI (2.18 g, 11.40 mmol), 1 – hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH; 1.90 mL, 13.30 mmol). The dark solution was stirred at rt overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M + H)+.

Statistics shows that 2-Amino-4-iodobenzoic acid is playing an increasingly important role. we look forward to future research findings about 20776-54-9.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

117832-17-4, Adding some certain compound to certain chemical reactions, such as: 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, 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 117832-17-4.

General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

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 117832-17-4.

Reference:
Article; Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua; Synlett; vol. 24; 17; (2013); p. 2315 – 2319;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

51560-21-5, The chemical industry reduces the impact on the environment during synthesis 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

In a 100.0mL Schlenk flask equipped with astir bar, 10 (0.2500 g, 0.641mmol), PdCl2(PPh3)2 (0.0442 g, 0.0632mmol), and CuI (0.3762 g, 1.976mmol) were added. A condenser was added, and the apparatus was purged andfilled with argon. Through the sidearm of the flask, 5.0mL of distilled triethylamine and 10.0mL of distilled toluene were added via a purged and filled airtight syringe. Lastly, 15mLof TMS acetylene was placed in a small round bottom flask and was degassed with argon for about 10 min before it was added through the sidearm of the Schlenk flask (0.1916 mL,1.346mmol) with a purged and filled airtight syringe. The apparatus was lowered into an 80C oil bath and heated for 24 hours. The solvent was removed from the light orange reaction mixture via rotary evaporation, and the solid was extracted with 10 mL of ethyl acetate and 10 minutes o fsonication. The remaining solid was removed via filtration,and the filtrate was rotovapped to produce crude product 11as a grayish/gold solid. The product was purified via MPLC on silica. The product eluted at 70 : 30 hexanes : ethyl acetate in quantitative yield. 1H NMR (500MHz, CDCl3) delta 0.21 (s,CH3, 18H), 3.76 (s, OCH3, 6H), 6.86 (s, Ph, 2H).

The chemical industry reduces the impact on the environment during synthesis 1,4-Diiodo-2,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Basinger, Corinne A.; Sullivan, Kaitlin; Siemer, Sarah; Oehrle, Stuart; Walters, Keith A.; Journal of Chemistry; vol. 2015; (2015);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com