Category: iodides-buliding-blocks

Synthetic Route of 811842-30-5, The chemical industry reduces the impact on the environment during synthesis 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, I believe this compound will play a more active role in future production and life.

Add QD105 (200g, 0.78mmol), 2-bromo-4-iodo-1-methylbenzene (457mg, 1.54mmol), potassium carbonate(323mg, 2.34mmol) and valine (18mg, 0.16mmol) to the eggplant In the flask, dimethyl sulfoxide was added, andthe reaction solution was deoxidized. Copper iodide (16 mg, 0.08 mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 256 mg.

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, 2-Bromo-1-fluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 391211-97-5,Some common heterocyclic compound, 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, molecular formula is C13H7F3INO2, 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.

Example 4. Preparation of N-((R)-2.3-dihydroxypropoxyV3.4-difluoro-2-(2-fluoro-4-iodo-phenylanriotainoV benzamide (Compound ) To a stirring solution of 3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzoic acid (9) (120 g, 0.30 mol) in a mixture of 1 mL N,N-dimethylformamide and 1000 mL toluene was added thionyl chloride (55 g, 0.462 mol). The mixture was heated to 50-65 C and stirred for 2 hours or until reaction completion as determined by HPLC (Conditions E). The final reaction mixture was then cooled and concentrated under reduced pressure to a slurry keeping the temperature below 35C. Toluene (600 mL) was added to dissolve the slurry and vacuum distillation was repeated. Additional toluene (600 mL) was added to the slurry dissolving all solids and the solution was then cooled to 5 -10C. The solution was then treated with O-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}hydroxylamine (6) (63 g, 0.43 mol) solution in 207 mL toluene followed by potassium carbonate (65 g) and water (200 mL), stirred for at least 2 hours at 20- 25C. The stirring was stopped to allow phase separation and the bottom phase was discarded. The remaining organic layer was treated with hydrochloric acid solution (7.4%, 240 mL) until pH was less than 1 and stirred for 2 hours. The final reaction mixture was slightly concentrated under vacuum collecting about 100 mL distillate and the resulting organic solution was cooled to 5C to crystallize the product and filtered. The filter cake was washed with toluene (1000 mL) followed by water (100 mL) and the wet cake (crude product Compound I) was charged back to the flask. Toluene (100 mL), ethanol (100 mL) and water (100 mL) are then added, stirred at 30-35C for about 15 min, and the bottom aqueous phase was discarded. Water (200 mL) was then added to the organic solution and the mixture was stirred at about 3O C to allow for crystallization. The stirring was continued for 2 hours after product crystallized, then it was further cooled to about 0C and stirred for at least 2 hours. The slurry was filtered and wet cake was dried under reduced pressure at 55-85C to yield the final product N-((R)-2,3-dihydroxypropoxy)-3,4- difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide (Compound I) product. Overall chemical yield was 86 g, 58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/134469; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-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

General procedure: To a solution of phenol 3 (0.45 mmol), aryl iodide 2 (0.45 mmol), ferrocenyl allene 1 (0.3 mmol) and Cs2CO3 (0.9 mmol) in MeCN (2.0 mL)was added Pd(PPh3)4 (0.015 mmol) under a N2 atmosphere. The resulting mixture was heated at 80 ¡ãC for 2 h. After completion of thereaction, the mixture was cooled to room temperature. The solvent was removed under vacuum, and the resulting residue was purified on a silica gel column (PE/EtOAc, 10:1) to provide the corresponding ferrocene-containing allylic ester product

The synthetic route of 1,3-Dichloro-5-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Xin-Xing; Wang, Chenjun; Zhao, Wanrong; Zhao, Haiying; Chen, Shufeng; Synthesis; vol. 50; 20; (2018); p. 4097 – 4103;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 3930-83-4, These common heterocyclic compound, 3930-83-4, name is 2-Iodobenzamide, 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: A two-neck round bottom flask was charged with amagnetic stirrer, evacuated and backfilled with argon. 2-iodobenzamide ( 0.5mmol, 124 mg), aniline or alpha-substituted benzylamine (1.0 mmol), K2CO3(1.0 mmol, 138 mg) and CuBr2 (0.05mmol, 11 mg) in DMSO (5 mL) under argon atmosphere. The mixture was allowed tostir under argon atmosphere at 110 C for 4 h.The mixture was concentrated with the aid of a rotary evaporator, and theresidue was purified by column chromatography on silica gel using petroleumether/ethyl acetate (2:1) as eluent to provide the product 2-9.

Statistics shows that 2-Iodobenzamide is playing an increasingly important role. we look forward to future research findings about 3930-83-4.

Reference:
Article; Wang, Li-Xia; Hu, Ben-Quan; Xiang, Jun-Feng; Cui, Jie; Hao, Xiang; Liang, Tong-Ling; Tang, Ya-Lin; Tetrahedron; vol. 70; 45; (2014); p. 8588 – 8591;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 202865-85-8, These common heterocyclic compound, 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, 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 solution of compound LXXXVI-1 (1.5 g, 4.9 mmol) in DME:H20 = 3: 1 (20 mL), Na2C03 (1.05 g, 9.9mmol) and compound LXXXVI-1A (1.47 mg, 4.9 mmol) were added, the resulting mixture was purged with nitrogen, then Pd (dppf)Cl2 (182 mg, 0.2 mmol) was added. The reaction mixture was stirred at 80 C overnight under nitrogen protection. After completion of the reaction, the mixture was poured into water, extract with EtOAc (30 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo. The residue was purified by chromatography (PE:EA = 100: 1) to afford compound LXXXVI-2 (1.06 g , yield 59.6%).

Statistics shows that 1-Bromo-4-iodo-2-methylbenzene is playing an increasingly important role. we look forward to future research findings about 202865-85-8.

Reference:
Patent; INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D.; WO2013/25733; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 112671-42-8

To a solution of 4-bromo-1-iodo-2-nitrobenzene (8.38 g, 109.6 mmol) in AcOH (45 mL) and EtOH(45 mL) at RT was added Fe (6.12 g, 109.6 mmol). The mixture was stirred at 100 C for 1.3 h andcooled to RT. The reaction mixture was diluted with Et2O (90 mL) and washed with sat. aq. NaHCO3(200 mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3 x 60 mL).The organic layers were combined, washed with brine (300 mL), dried over Na2SO4, and concentrated invacuo. The residue was purified by flash chromatography (silica gel, hexane/AcOEt = 19:1) to afford 5-bromo-2-iodoaniline 30b (6.89 g, 91% yield) as a light yellow solid.

The synthetic route of 112671-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Miyamoto, Hiroshi; Hirano, Tomohiro; Okawa, Yoichiro; Nakazaki, Atsuo; Kobayashi, Susumu; Tetrahedron; vol. 69; 45; (2013); p. 9481 – 9493;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

68507-19-7, name is 3-Iodo-4-methoxybenzoic 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 68507-19-7

Methyl 3-iodo-4-methoxybenzoate (29.2 g, 0.1 mol) was suspended in EtOH (150 mL), the solution of NaOH (4.4 g, 0.11 mol) was added in one portion. The mixture was stirred and heated at 40C overnight, then cooled, diluted with water (400 mL). 3-Iodo-4-methoxybenzoic acid was precipitated with conc. HCl, filtered off, washed with cold water, and dried over P4O10. The acid was suspended in CHCl3 (150 mL), and SOCl2 (9.5 mL, 0.13 mmol) was added. The mixture was stirred overnight, then evaporated and the residue was distilled under reduced pressure to give the desired acid chloride as a solid (mp ca. 50C, bp 145-150C/1 Torr). Yield 18.2 g (61%).

The synthetic route of 68507-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OXFORD GENE TECHNOLOGY IP LIMITED; EP1506959; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 138385-59-8, A common heterocyclic compound, 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride, molecular formula is C8H11ClIN, 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.

A 2 L round bottom flask was charged 4-iodo-2,6-dimethylbenzenamine hydrochloride salt (55 g, 194 mmol), methyl 2-(benzyloxycarbonyl)acrylate (59.2 g, 252 mmol), tetrabutylammonium chloride (59.2 g, 213 mmol), palladium (II) acetate (4.34 g, 19.4 mmol), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred so that a suspension was formed and then degassed by a flow of nitrogen for 30 min. Triethylamine (10 mL, 789 mmol) was added and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, washed with tetrahydrofuran (2¡Á100 mL), and concentrated. The residue was dissolved in dichloromethane, washed with water (3¡Á) and brine (2¡Á), dried over sodium sulfate, and concentrated. Flash chromatography (silica gel using 1:9 ethyl acetate/dichloromethane) gave a tan solid. The solid was recrystallized from warm methanol (210 mL) and water (100 mL). The mixture was held at room temperature overnight, then at 0 C. for 2 h, and finally at -15 C. for 2 h. The resulting solid was filtered, washed with ice cold 1:1 methanol/water, and dried under high vacuum overnight to give 44.7 g (65%) as a light tan solid which was a mixture of Z/E isomers (73:27). 1H-NMR (DMSO-d6) 6, 2.05 (s, 6H), 3.61 (s, 0.8H), 3.68 (s, 2.2H), 5.00 (s, 0.54H), 5.13 (s, 1.46H), 5.24 (s, 2H), 7.40-7.21 (m, 8H), 8.51 (s, 0.27H), 8.79 (s, 0.73H); 13C-NMR (DMSO-d6) delta 17.8, 51.7, 65.3, 119.4, 120.0, 120.3, 127.3, 127.7, 128.3, 130.9, 135.8, 137.2, 146.9, 154.7, 166.0.

The synthetic route of 138385-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chaturvedula, Prasad V.; Han, Xiaojan; Jiang, Xiang-Jun J.; US2006/122250; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 3930-83-4, A common heterocyclic compound, 3930-83-4, name is 2-Iodobenzamide, molecular formula is C7H6INO, 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 10 mL reaction tube were added MCM-41-L-Proline-CuBr(135 mg, 0.1 mmol), 2-halobenzamide 1 (1.0 mmol), benzylamine derivative 2 (2.0 mmol), K2CO3 (3.0 mmol), and DMSO (3 mL). The reaction mixture was stirred at 110 or 120 C under air for 6-12 h.After being cooled to room temperature, the reaction mixture was diluted with 20 mL of EtOAc, and filtered. The MCM-41-L-Proline-CuBr complex was washed with distilled water (2 5 mL) and ethanol (2 5 mL), and reused in the next run. The filtrate was washed with water (2 10 mL) and dried over MgSO4. After being concentrated in vacuo, the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc 3:1 to 2:1)to afford the target product 3.

The synthetic route of 3930-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Nan; You, Chongren; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 897; (2019); p. 161 – 169;,
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. 39959-51-8, name is (2-Iodophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 39959-51-8

Example 14 N4-[(trans-4-aminocyclohexyl)methyl]-N2-{2-[(2-aminophenyl)thio]benzyl}-5-nitropyrimidine-2,4-diamine To a solution of {4-[(2-chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (100 mg, 0.26 mmol) in a mixture of CH2Cl2 (2 mL) and DMF (1 mL) were added 2-iodobenzylamine (192 mg, 0.82 mmol) and DIPEA (135 muL, 1.04 mmol). The reaction mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was diluted with EtOAc and washed with water (*3) and then with brine. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 97 mg (64%) of (4-{[2-(2-iodo-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester.

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; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com