Category: iodides-buliding-blocks

Synthetic Route of 88-82-4, 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. 88-82-4 name is 2,3,5-Triiodobenzoic acid, 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.

[0251] Several approaches have been used to synthesize iodine-containing X-ray contrast agents. The esterification of the ethanolamide of indomethacin has been accomplished by carbodiimide coupling of indomethacin ethanolamide (Compound 4) and 2,3,5-triiodobenzoic acid (FIG. 7). The product, Compound 5, is a potent and highly selective COX-2 inhibitor (IC50 for COX-2=50 nM, IC50 for COX-1>50 muM). Higher concentrations are required for inhibition of COX-2 in the RAW264.7 macrophage cell line (IC50=3.5 muM), which might be related to the hydrophobicity of the compound (cLogP=8.5). Amide derivatives (Compounds 8 and 9) that correspond to the ester, Compound 5, are generated. Compounds 6 and 7 are synthesized and their coupling to 2,3,5-triiodobenzoic acid is carried out

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3,5-Triiodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; US2005/2859; (2005); A1;,
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. 14452-30-3, name is 1-(3-Iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 14452-30-3

To a stirred solution of l-(3-iodophenyl) ethanone 22-1 (200 mg, 0.81 mmol) in DMF (3 mL) was added allyl alcohol (252 mg, 4.06 mmol), AgOAc (137 mg,0.81 mmol), TPP (21 mg, 0.081 mmol). The mixture was purged with argon for 15 min and Pd(OAc)2 (27 mg, 0.04 mmol) was added at RT. The reaction mixture was warmed to 70 C for 16 hr under nitrogen atmosphere. The reaction mixture was diluted with water (10 mL) extracted with EtOAc (3 X 50 mL), the combined organic layers were washed with brine (2 X 40 mL) and dried over Na2S04 and concentrated. The residue was purified by column chromatography (100-200 silica) using 20-25% EtOAc/Pet. ether to afford 22-2 (100 mg, 0.56, 69.9% yield) as a colorless liquid. MS=177.1 [M+l]+.

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 14452-30-3.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina C.; FEESE, Michael D.; LEE, Sam S.; (169 pag.)WO2016/154241; (2016); A1;,
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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., category: iodides-buliding-blocks

2-Ethoxyethylamine (2.14g, 24mmol) and diisopropylethylamine (4. 2ml, 24mmol) were dissolved in DCM (sol) and cooled to 0 C. To this was added pipsyl chloride (6.05g, 20mmol) in portions and the reaction stirred for 18 hours. Volatiles were evaporated in vacuo. The residue was dissolved in EtOAc (sol), washed with 0.33M citric acid (2 x 50ml), brine (sol), dried and evaporated in vacuo to yield an oil which solidified on standing to give the title compound as a pale yellow solid (6.97g, 98%). NMR: 1.01 (t, 3H), 2.89 (q, 2H), 3.30 (m, 4H), 7.53 (d, 2H), 7.75 (t, 1H), 7.97 (d, 2H); m/z 354 (M-H)-.

According to the analysis of related databases, 98-61-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/76436; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5471-81-8,Some common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, molecular formula is C9H9IO2, 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.

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10mol%),Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),1,2-epoxyhexane (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred for 24 hours. Time. After the reaction vessel was cooled to room temperature, it was diluted with water (10 mL). Filter and concentrate under vacuum. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 20:1 (v/v).35 mg of methyl 7-methyl-2-n-butyl-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 71%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-iodo-3-methylbenzoate, its application will become more common.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
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. 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-iodo-2-methoxybenzene

To a solution of 4-bromo-1-iodo-2-methoxybenzene (1.634 g, 5.221 mmol) in dry acetonitrile (20 mL) Cul (49.7 mg, 0.261 mmol) and Pd(Ph3P)2Cl2 (183.2 mg, 0.261 mmol) were added under Argon atmosphere and the mixture was degassed and backfilled with Argon for three times. TEA (0.728 mL, 5.221 mmol) and (ethynyl)trimethylsilane(l .48 mL, 1.03 g, 10.442 mmol) were added with a syringe and the reaction mixture, that darkened within 10 min, was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was taken up with EtOAc (100 mL), washed with brine (3 x 20 mL), water (20 mL), dried over sodium sulphate and evaporated to dryness. The crude was purified by chromatography on silica gel (petroleum ether/diethyl ether 9/1) to yield the title compound as an orange solid (1.426 g, 96.5%). 1H NMR (400 MHz, DMSO-cie) delta ppm 0.21 (s, 9 H) 3.83 (s, 3 H) 7.11 (dd, J=8.18, 1.83 Hz, 1 H) 7.26 (d, J=1.83 Hz, 1 H) 7.31 (d, J=8.06 Hz, 1 H).

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; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (2013); A1;,
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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4FIO2

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).

According to the analysis of related databases, 52548-63-7, the application of this compound in the production field has become more and more popular.

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

Application of 75581-11-2, 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 75581-11-2 as follows.

General procedure: A DMF solution (8mL) of the o-substituted aryl iodide (0.36mmol), the o-bromobenzyl alcohol (0.36mmol) and norbornene (34mg, 0.36mmol) was added under nitrogen to a Schlenck-type flask, containing Pd(OAc)2 (4mg, 0.018mmol), the phosphine (0.036mmol), when required, and K2CO3 (124mg, 0.90mmol) or CsOPiv (211mg, 0.90). The reaction mixture was stirred at 105C for 24h. After cooling to room temperature the organic layer was diluted with EtOAc (20mL), washed twice with water (20mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using mixtures of hexane-EtOAc as eluent.

According to the analysis of related databases, 75581-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Della Ca, Nicola; Fontana, Marco; Xu, Di; Cremaschi, Mirko; Lucentini, Riccardo; Zhou, Zhi-Ming; Catellani, Marta; Motti, Elena; Tetrahedron; vol. 71; 37; (2015); p. 6389 – 6401;,
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 624-75-9 as follows. Safety of 2-Iodoacetonitrile

General procedure: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
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. 619-58-9, name is 4-Iodobenzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 619-58-9

Step A — Preparation of p-iodobenzyl alcohol To a stirred solution of p-iodobenzoic acid (5 mmole) in a dry tetrahydrofuran (20 ml) at -70 is added a suspension of lithium aluminum hydride (10 mmole) in tetrahydrofuran (10 ml). The mixture is allowed to warm to 0 and stirred at 0 for 2 hours. The reaction mixture is then poured into a dilute hydrochloric acid — ice mixture and extracted with ether. The ether extract is washed with dilute bicarbonate solution, washed, dried over sodium sulfate and concentrated to dryness. Chromatography of the residue on a silica gel gives p-iodobenzyl alcohol.

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; Merck & Co., Inc.; US4064236; (1977); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 63131-30-6, The chemical industry reduces the impact on the environment during synthesis 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, I believe this compound will play a more active role in future production and life.

Preparation of ethyl 3-(4-iodophenyl)-3-(phenylamino)acrylate 24[00332]To a solution of aniline (2.93g, 2.86ml, 31.4mmol) in EtOH (10ml), acetic acid (1.89g, 1.80ml, 31.4mmol) was added, followed by the addition of a solution of ethyl (4-iodobenzoyl) acetate in EtOH (10ml). The resulting solution was heated to reflux for at least 4 hours. EtOH was removed in vacuo, and the residue dissolved in DCM. The DCM solution was then washed with water, 5%HCl(aq.) and brine, and dried with Na2S04. The DCM was removed in vacuo to give the crude product as a yellow solid. The crude product was purified by columnchromatography eluting with 5% EtOAc in hexane to give the title product (1.06, 86%) as a pale yellow crystalline solid. 1H NMR (400 MHz, CDC13) delta 10.23 (s, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.17 – 7.02 (m, 5H), 6.94 (t, J = 6.9 Hz, 1H), 6.66 (d, J = 7.5 Hz, 2H), 4.97 (s, 1H), 4.20 (q, J = 7.1 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 3-(4-iodophenyl)-3-oxopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIVERPOOL SCHOOL OF TROPICAL MEDICINE; O’NEILL, Paul; BIAGINI, Giancarlo; WARD, Stephen A.; BERRY, Neil Graham; NIXON, Gemma; AMEWU, Richard K.; PIDATHALA, Chandrakala; HONG, Weiqian David; GIBBONS, Peter; LEUNG, Suet Ching; PACOREL, Benedicte; SHARMA, Raman; LAWRENSON, Alexandre S.; SHONE, Alison E.; SRIVASTAVA, Abhishek; WARMAN, Ashley J.; WO2012/69856; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com