Author: Jessica.F

Related Products of 452-79-9,Some common heterocyclic compound, 452-79-9, name is 2-Fluoro-1-iodo-4-methylbenzene, molecular formula is C7H6FI, 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.

A mixture of 3-fluoro-4-iodotoluene (2.26 g, 9.58 mmol), N-bromosuccinimide (2.03 g, 11.49 mmol) and benzoyl peroxide (5 mol %, 116 mg, 0.48 mmol) in carbon tetrachloride (5 ml) was stirred at reflux for 20 hours, cooled, diluted with dichloromethane and filtered. The purple coloured filtrate was washed with saturated sodium thiosulphate solution (aq) (20 ml). The organic layer was separated, dried over sodium sulphate and the solvent removed by rotary evaporation to give the title compound as a yellow oil (2.58 g, 86%).1H-NMR (250 MHz, CDCl3): delta 7.72 (1H, m), 7.11 (1H, m), 6.94 (1H, m), 4.41 (2H, s).

The synthetic route of 452-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2010/137276; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, 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 52548-63-7

To a solution of 1H-pyrrolo[2,3-c]pyridine (70 g, 0.59 mol) in MeOH (1,050 mL) and H2O (350 mL) was added KOH (83 g, 1.48 mol) and tert-butyl 3-oxopiperidine-1- carboxylate (259 g, 1.30 mol). The resulting mixture was stirred at 75-80 oC (oil bath temperature) for 18 h. The reaction mixture was concentrated under reduced pressure to remove MeOH, then H2O (700 mL) was added and the mixture was extracted with EtOAc (3 ¡Á 1000 mL). The organic layers were filtered and the filtered cake was washed with EtOAc (2 ¡Á 150 mL) to afford tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (75 g, 42% yield) as white solid. The organic layer was concentrated under reduced pressure to about 250 mL. The residue was stirred at 5-9 oC for 18 h. The residue was filtered and the filtered cake was washed with EtOAc (2 ¡Á 60 mL) to give a mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6- dihydropyridine-1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4- dihydropyridine-1(2H)-carboxylate (1:3.5 via LCMS; (28 g, 16% yield) as white solid. tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine-1(2H)- carboxylate: Yield: 75 g (42%); Rt value: 0.570 (LCMS Method C); (M+H)+ = 300.1; 1H NMR (MeOD, 400 MHz): delta ppm 8.65-8.70 (d, J = 2.8 Hz, 1H), 8.05-8.15 (d, J = 5.6 Hz, 1H), 7.70-7.90 (m, 1H), 7.54 (s, 1H), 7.35-7.50 (m, 1H), 3.60-3.75 (m, 2H), 2.50-2.60 (t, J = 5.6 Hz, 2H), 2.00-2.10 (m,2H), 1.55-1.60 (m, 9H). Mixture of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate: Rt value: 0.568 (LCMS Method C); (M+H)+ = 300.1. A suspension of tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine- 1(2H)-carboxylate and tert-butyl 5-(1H-pyrrolo[2,3-c]pyridin-3-yl)-3,6-dihydropyridine- 1(2H)-carboxylate (1 g, 3.34 mmol, ~10:1 ratio of isomers), 5-fluoro-2-iodobenzoic acid (977 mg, 3.67 mmol), K2CO3 (1.15 g, 8.33 mmol), CuI (63 mg, 0.334 mmol) and 1,10- phenanthroline (60 mg, 0.334 mmol) in DMF (13 mL, 0.26 M reaction concentration) was degassed with N2 for 15 min. The reaction mixture was then placed under N2 and heated to 70 oC for 24 h. The reaction was then cooled to room temperature and filtered through a plug of Celite using a small amount of DMF to rinse the filter cake. The DMF solution was cooled to 0 oC and a 1N aq. HCl solution (~10 mL) was added, maintaining a pH of ~5, followed by the addition of H2O (~10 mL) and EtOAc for the extraction. The EtOAc layer was separated and the aqueous layer (pH~5) was extracted three additional times with EtOAc. The EtOAc layers were combined and washed with H2O followed by brine. After drying over Na2SO4, the EtOAc layer was evaporated and the resulting residue was dried under high vacuum overnight to afford ~2 grams of crude 2-(3-(1-(tert-butoxycarbonyl)-1,4,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-c]pyridin- 1-yl)-5-fluorobenzoic acid and 2-(3-(1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridin-3- yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)-5-fluorobenzoic acid (>10:1 ratio of isomers). The crude material was used directly for the next step without further purification. LCMS: 5.748 min (LCMS Method G): 438.47 (M + 1).1H NMR (400 MHz, CDCl3): delta 8.52-8.48 (m, 1H), 8.20-8.15 (m, 1H), 8.07 (bs, 1H), 8.01 (s, 1H), 7.85 (d, 1H, J = 8.4 Hz), 7.76 (s, 1H), 7.55 (bs, 1H), 7.42 (d, 1H, J = 5.2 Hz), 3.67 (bs, 2H), 2.50-2.47 (m, 2H), 2.06-2.01 (m, 2H), 1.54 (s, 9H). To a solution of the crude mixture from Step 2, (3.34 mmol), N-methylpropan-2- amine (731 mg, 10.02 mmol) and iPr2NEt (1.74 mL, 10.02 mmol) in EtOAc (9 mL) was added a 50 wt% solution of T3P in EtOAc (6 mL, 10.02 mmol) dropwise at ~10 oC. The reaction was stirred for 2 h, cooled to 0 oC, and a 1N aq. NaOH solution (~10 mL) was slowly added. The EtOAc layer was separated and the aqueous layer was extracted twice with EtOAc. The EtOAc layers were combined and washed with sat. NH4Cl, H2O, and then brine. After drying over Na2SO4, the EtOAc layer was evaporated to afford 1.65 grams of crude tert-butyl 5-(1-(4-fluoro-2-(isopropyl(methyl)carbamoyl)phenyl)-1H- pyrrolo[2,3-c]pyridin-3-yl)-3,4-dihydropyridine-1(2H)-carboxylate (purity: ~90% based on LCMS analysis). This material was used directly for the next step without further purification. LCMS: 6.247 min (LCMS Method G); 493.55 (M+1).1H NMR (400 MHz, CDCl3) The title compound was observed as a mixture of rotamers by NMR, the major rotamer isomer peaks were tabulated and are provided: delta 8.07-8.68 (m, 1H), 8.35-8.32 (m, 1H), 7.88 (d, 1H, J = 5.2 Hz), 7.62 (bs, 1H), 7.55-7.52 (m, 1H), 7.43-7.41 (m, 1H), 7.29-7.18 (m, 2H), 4.65-4.75 (m, 1H), 3.60-3.65 (m, 2H), 2.69 (s, 3H), 2.40-2.45 (m, 2H), 1.90-2.00 (m, 2H), 1.57 (s, 9H), 0.95-0.94 (m, 3H), 0.56-0.59 (m, 3H).

The synthetic route of 52548-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

7681-82-5, name is Sodium iodide, 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. Recommanded Product: 7681-82-5

General procedure: A typical example is exemplified by the synthesis of 4b: To a stirred solution of TMEDA (1.36 mL,9 mmol) in hexane (5 mL) was added dropwise at ice bath temperature n-butyllithium (9 mmol) in hexane followed by acetophenone trimethylsilyl enol ether 1 (576 mg, 3 mmol), and the mixture was stirred for 24 h at room temperature. In a separate flask, a mixture of bismuth(III) chloride (315.5 mg,1 mmol) and tris(4-methylphenyl)bismuthane (964 mg, 2 mmol) was stirred in ether (10 mL) at room temperature for 1 h. To the suspension of chlorobis(4-methylphenyl)bismuthane (ca. 3 mmol) thus formed was added sodium iodide (450 mg, 3 mmol) and a few drops of 15-crown-5 ether and the resulting yellowish mixture was stirred for 3 h at room temperature. To a suspension of the lithium compound previously prepared was added at room temperature magnesium dibromide diethyl etherate (775 mg, 3 mmol) followed by, at -30 C, a suspension of iodobis(4-methylphenyl)bismuthane(ca. 9 mmol), and the resulting mixture was stirred for 1 h, during which time the temperature was raised to ambient temperature. The reaction mixture was poured into brine (50 mL) and extracted with ethyl acetate (50 mL ¡Á 3). The combined extracts were concentrated to leave an oily residue, which was purified by chromatography (silica gel) using hexane-ethyl acetate (5:1) as the eluent to afford 4b in 30% yield (459 mg, 0.9 mmol). Because 4a, 4f and 10 underwent decomposition when purified by chromatography on silica gel, these compounds were converted into the corresponding halobismuthanes 5a, 5f and 11, respectively, without isolation.

The synthetic route of 7681-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Murafuji, Toshihiro; Tomura, Mai; Ishiguro, Katsuya; Miyakawa, Isamu; Molecules; vol. 19; 8; (2014); p. 11077 – 11095;,
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. 32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Iodo-4,5-dimethoxybenzaldehyde

3, 4-dimethoxy-5-iodo-benzaladehyde (2.92 g, 10 mmol) wasdissolved in minimal EtOH and stirred in an ice bath. After the entire solid had dissolved NaBH4 (3.4 g,~10 mmol) was added to the mixture. The progress was monitored by HPLC. After, 1.5 hours thecomplete reaction mixture was concentrated under vacuum to half its volume and poured into aseparating funnel containing water. Aqueous layer was extracted three times with DCM. It was thenconcentrated to give the final product as yellow oil (2.79 g, 9.5 mmol). 1H NMR (300 MHz, DMSO-d6): 7.40 – 7.27 (m, 1H), 7.02 (d, J = 1.7 Hz, 1H), 4.53 (s, 2H), 3.87 (s, 3H), 3.77 (s, 3H). UV-Vis: 214.7, 285.1nm.

According to the analysis of related databases, 32024-15-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Maresh, Justin J.; Ralko, Arthur A.; Speltz, Tom E.; Burke, James L.; Murphy, Casey M.; Gaskell, Zachary; Girel, Joann K.; Terranova, Erin; Richtscheidt, Conrad; Krzeszowiec, Mark; Synlett; vol. 25; 20; (2014); p. 2891 – 2894;,
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. 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane

In a 20 liter reaction vessel, 1500 g (3.16 mol) of 1H, 1H, 2H, 2H-perfluorohexylethyl iodide and 3 L of dimethylformamide were added, and 230 g (3.5 mol) of sodium azide was added. The mixture was stirred at room temperature for 3 h, GC showed complete conversion, selectivity 99%, water 3 L, allowed to stand, layered, the aqueous layer was washed three times with methyl tert-butyl ether,The three washed organic layers were washed three times with brine to give crude 1H, 1H, 2H, 2H-perfluorooctyl azide containing methyl tert-butyl ether.

According to the analysis of related databases, 2043-57-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Juhua Group Technology Center; Wang Zhiguang; Jiang Yun; (6 pag.)CN106278921; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, 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 689291-89-2, Quality Control of 5-Bromo-2-iodobenzaldehyde

To an ice-cold solution of 2,2,5, 5-tetramethyldihydrofuran-3-one (0.388g, 2.73mmoles) in anhydrous 1 ,2-diotamethoxyethane (5ml) is added sodium methoxide (0.177g, 3.27mmoles) in one portion. The reaction mixture is stirred for 5 minutes at this temperature, followed by the dropwise addition of 5-bromo-2-iodo-benzaldehyde (0.85Og, 2.73mmoles) as a solution in 1 ,2-dimethoxyethane (5ml). The reaction mixture is further stirred at O0C for 30 minutes, then at ambient temperature for a 1 hour. After partitioning between 1 M hydrochloric acid and dichloromethane, the organic phase is separated, and the aqueous phase is extracted again with additional dichloromethane. All organics are combined then concentrated in vacuo to afford 4-[1-(5-bromo-2-iodophenyl)methyliotadene]-2,2,5,5-tetramethyldihydrofuran-3-one(1.18g) as a yellow gum.

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; SYNGENTA LIMITED; SCUTT, James Nicholas; WO2010/136431; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 83171-49-7, 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. 83171-49-7 name is 3-Chloro-5-iodoaniline, 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.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-iodoaniline, and friends who are interested can also refer to it.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 98-61-3, A common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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: C5-Arylated Furans; General Procedure To a 25-mL oven-dried Schlenk tube, arenesulfonyl chloride (1.5-2 mmol), furan derivative (1 mmol), Li2CO3 (0.222 g, 3 mmol), 1,4-dioxane (2 mL) and PdCl2(MeCN)2 (12.9 mg, 0.05 mmol) wereadded successively. The mixture was evacuated by vacuum-argoncycles (5 ) and stirred at 140 C (oil bath temperature) for 20-72 h(see tables and schemes). After cooling the reaction at r.t. and con-centration, the crude mixture was purified by column chromatogra-phy (silica gel) to afford the C5-arylated furans.

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; Beladhria, Anissa; Yuan, Kedong; Ben Ammar, Hamed; Soule, Jean-Francois; Ben Salem, Ridha; Doucet, Henri; Synthesis; vol. 46; 18; (2014); p. 2515 – 2523;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 21740-00-1, name is 5-Bromo-2-iodobenzoic 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 21740-00-1, Computed Properties of C7H4BrIO2

General procedure: A sealed tube was charged with CuCl (0.02 mmol), BFMO (0.02 mmol), N-protected N-alkenylhydrazine (2.0 mmol), 2-iodobenzoic acid (2.4 mmol), and K2CO3 (4 mmol). The tube was evacuated and backfilled with argon three times before anhydrous DMSO (4.0 mL) was added via syringe (NOTE: for liquid substrates, they were added into the tube via syringe after the tube was backfilled with argon). The mixture was sealed and stirred at 80 C for 24 h. The mixture was diluted with EtOAc, washed with water, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated in vacuo and the residue was treated with 4M HCl/1,4-dioxane (1.2 mL) at 80 C. After the starting material was completely consumed, the solution was cooled and diluted with EtOAc. The resultant mixture was washed with water and dried over anhydrous sodium sulfate. After the solution was concentratedin vacuo, the residue was purified by flash chromatography to afford the corresponding indole.

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:
Article; Wei, Quanpeng; Wang, Yunhan; Zhao, Jinlong; Zhang, Xiaojing; Ma, Dawei; Tetrahedron; vol. 76; 1; (2020);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 124700-41-0, These common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, 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.

Preparation 29 Ethyl 3-(2-fluoro-5-iodophenyl)-3-oxopropanoate To a stirred solution of 5.32 g of 2-fluoro-5-iodobenzoic acid from Preparation No. 28 in 20 mL of THF, under argon, is added 3.9 g of carbonyldiimidazole. In a separate flask, 2.8 mL of chlorotrimethylsilane is added to a mixture of 3.74 g of potassium ethyl malonate in 20 mL of acetonitrile. The mixture is stirred under argon for 18 h, then cooled to 0 C. for the dropwise addition of 6.6 mL of DBU. The mixture is stirred for 3 h at 0 C., then the solution of acyl imidazolide prepared above is added via cannula. After 2 h, the mixture is partitioned between ether and excess dilute HCl, and the organic phase is washed with dilute HCl and brine and dried (MgSO4). Removal of the solvent under reduced pressure left a colorless oil, which is flash chromatographed on silica using 10% ethyl acetate in hexane to provide 5.07 g of the title compound as dense pinkish prisms. Physical properties as follows: 1H NMR (CDCl3) delta1.34, 4.27, 5.82, 6.89, 7.7, 8.2 ppm; IR 1624, 1485, 1419, 1245, 1193, 1070, 1028, 813 cm-1.

Statistics shows that 2-Fluoro-5-iodobenzoic acid is playing an increasingly important role. we look forward to future research findings about 124700-41-0.

Reference:
Patent; Pharmacia & Upjohn Company; US6248739; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com