Month: August 2021

Synthetic Route of 628-21-7,Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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.

Making reference to Scheme 10, to a solution of 5-(3,4,5-trimethoxyphenyl)-l- ((2-(trimethylsilyl)ethoxy)-methyl)- lH-pyrrolo[2,3-£]pyridin-2(3H)-one (Intermediate D, 43 mg, 0.10 mmol) in DMF (2 mL) was added cesium carbonate (0.17 g, 0.50 mmol) and 1,4-diiodobutane (13 mu, 0.10 mmol). The resulting solution was stirred for 4 hr at room temperature, after which it was partitioned between EtOAc and 0. The organic layer was separated, dried over MgS04, filtered, and concentrated in vacuo. The residue was dissolved in 6 N HCI (10 mL) and MeOH (5 mL), and the resulting mixture was stirred at room temperature overnight, after which it was partitioned between EtOAc and 0. The organic layer was concentrated in vacuo, and the residue was dissolved in EtOH (2 mL). Potassium acetate (100 mg) was then added, and the reaction was stirred for 2 hr. The resulting solution was purified via preparatory HPLC to give the title compound (18 mg, 51%). ^ MR CCDCls, 300 MHz): delta 9.53 (s, 1H), 8.32 (d, J= 2.1 Hz, 1H), 7.56 (s, 1H), 6.69 (s, 2H), 3.95 (s, 6H), 3.90 (s, 3H), 2.28 (m, 2H), 2.24 (m, 2H), 1.97 (m, 4H). HPLC retention time: 2.00 minutes; MS ESI (m/z): 355.4 (M+l) +, calc. 354.

The synthetic route of 628-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF ROCHESTER; BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA; GELBARD, Harris A.; DEWHURST, Stephen; GENDELMAN, Howard E.; WO2014/85795; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 21304-38-1, name is 4-Iodobenzene-1,2-diamine, 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 21304-38-1, SDS of cas: 21304-38-1

4-Iodo-l,2- phenylenediamine (0.47 g) and 3-(2-naphthyl)glutaric anhydride (0.48 g) were dissolved in dichloromethane (6 ml) with heating. The dark solution was stirred at rt for 1 h. The precipitate formed was collected by suction filtration, washed with dichloromethane, and dried in vacuo to give a mixture of regioisomeric amides (0.82 g) as light red solid. This solid was dissolved in 4M HCI in 1,4-dioxane (3 ml) and the dark solution was heated to reflux for 1 h. The precipitate formed is isolated by suction filtration of the still hot mixture and washed with 1,4-dioxane, hot acetic acid, and finally diethyl ether to provide 4-(5-iodo-2-benzimidazolyl)-3- (2-naphthyl)butanoic acid HCI (0.71 g) as light red solid. 1H-NMR (500 MHz, DMSOd6)): delta (ppm) = 2.83 (dd, J = 16.1, 8.3 Hz, IH), 2.91 (dd, J = 16.1, 6.4 Hz, IH), 3.57 (dd, J = 14.9, 9.1 Hz, IH), 3.64 (dd, J = 14.9, 7.0 Hz, IH), 4.02 (m, IH), 7.45 (m, 2H), 7.51 (dd, J = 8.6, 2.4 Hz, 2H), 7.72 (dd, J = 8.6, 1.5 Hz, IH), 7.82 (m, 4H), 8.06 (d, J = 1.4 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 32.64 (CH2), 39.93 (CH2), 39.96 (CH), 89.44 (C), 115.64 (CH), 121.99 (CH), 125.53 (CH), 125.60 (CH), 125.70 (CH), 126.06 (CH), 127.34 (CH), 127.48 (CH), 128.01 (CH), 130.49 (C), 131.96 (C), 132.57 (C), 132.75 (C), 133.67 (CH), 139.23 (C), 152.73 (C), 172.25 (CO).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodobenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 49827-15-8, A common heterocyclic compound, 49827-15-8, name is tert-Butyl 2-iodoacetate, molecular formula is C6H11IO2, 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.

Analogously to Example 154, the compounds of Table 14 were produced

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; Schering Aktiengesellschaft; US6344454; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13421-00-6, A common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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.

5-Chloro-2-iodobenzoic acid (2.8 g, 10 mmol) was taken up in dry methylene chloride (80 mL) and DMF (50 muL, cat.) followed by thionyl chloride (2.4 g, 20 mmol) were added. The mixture was stirred at reflux for 12 h, cooled to room temperature and evaporated in vacuo. The residue was azeotroped with toluene (2×10 mL) and used without further purification. The 5-chloro-2-iodobenzoyl chloride (10 mmol) was taken up in dry methylene chloride (50 mL) and N,O-dimethylhydroxylamine hydrochloride (1.1 g, 11 mmol) was added. The mixture was cooled to 0 C., and pyridine (2.4 g, 30 mmol) was added. The mixture was allowed to warm to room temperature, stir for 12 h, and was then quenched with saturated brine (20 mL). The organic phase was separated and the water phase was extracted with methylene chloride (2×10 mL). The combined organic extracts were dried with anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified using flash chromatography on silica gel (50 g) using methylene chloride as eluent to provide 5-chloro-2-iodo-N-methoxy-N-methylbenzamide (3.1 g, 95%) MS m/z=326 (M+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; Millennium Pharmaceuticals, Inc.; US2005/256102; (2005); 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. 5326-47-6, name is 2-Amino-5-iodobenzoic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-5-iodobenzoic acid

a) 2-Amino-5-iodo-benzoic acid methyl ester; 2-Amino-5-iodo-benzoic acid (10.00 g) was dissolved in methanol (200 ml_). To this solution, Amberlist-15 (16.00 g) was added and the resulting mixture was heated under reflux under nitrogen for 48 h. After cooling to room temperature the mixture was filtered and the solid was washed with 5% 2OM ammonia/MeOH (2 x 100 ml_). The organic phase was dried and the solvent evaporated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate / hexane from 1 / 15 to 1 / 12) to give the title compound (7.00 g); ESMS m/z 277.9 [M+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; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50943; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7, The chemical industry reduces the impact on the environment during synthesis 618-91-7, name is Methyl 3-iodobenzoate, I believe this compound will play a more active role in future production and life.

General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. 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, Methyl 3-iodobenzoate, other downstream synthetic routes, hurry up and to see. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 628-21-7, A common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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 suspension of 4-amino-5-fluoropyrimidin-2-ol (0.50 g, 3.87 mmol) in acetonitrile (CH3CN; 20 mL) was added BSA (1.58 g, 7.75 mmol), and the mixture was heated to 70 0C for 1 h resulting in a clear solution. After cooling to room temperature, 1,4-diiodobutane (1.2 g, 3.87 mmol) was added, and the mixture was stirred for 16 h at room temperature and then at 70 0C for 3 h. The solvent was evaporated and the residue was purified by normal phase chromatography (24 g SiO2; gradient, 0 to 15% MeOH/CH2Cl2) to give an orange oil. The oil was dissolved in EtOAc and the solution was slowly cooled. The resulting solid was collected by filtration, washed with additional EtOAc, and dried to give 4-amino-5-fluoro-l- (4-iodobutyl)-lH-pyrimidin-2-one (0.52 g, 43%) as a tan solid: mp 181-184 0C; 1H NMR (400 MHz, DMSO-J6) delta 8.56 (s, 2H), 8.25 (d, / = 6.7 Hz, IH), 3.70 (t, /= 6.7 Hz, 2H), 3.29 (t, / = 6.7 Hz, 2H), 1.73 (m, 4H); ESIMS m/z 312 ([M+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; DOW AGROSCIENCES LLC; BOEBEL, Timothy; BRYAN, Kristy; JOHNSON, Peter; LORSBACH, Beth; MEYER, Kevin; OWEN, W.; SULLENBERGER, Michael; WEBSTER, Jeffery; YAO, Chenglin; WO2011/17540; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 153898-63-6, 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. 153898-63-6, name is 2-Iodo-5-methoxyaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of o-iodoaniline (0.5 mmol, 1 equiv), arylacetic acid (0.6 mmol), elemental sulfur (1.5mmol), Cu(OAc)2·H2O (20 mmol%), and NaOH (1.0 mmol) in DMSO (3 mL) was put into a sealed pressure vessel (25 mL) containing a magnetic stirring bar. The tube was purged with nitrogen three times, and then capped and stirred in a preheated oil bath at 130 C for 24 h. The reaction mixture then cooled to room temperature and extracted with ethyl acetate (3×10 mL), the organic layer was washed with saturated NaCl (2×10 mL), dried over anhydrous Na2SO4, evaporated under vacumm and then purified by silica gel column chromatography by using petroleum ether and ethyl acetate (PE:EA=200:1) as eluent.

The synthetic route of 2-Iodo-5-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xin; Li, Xiaotong; Hu, Renhe; Yang, Zhao; Gu, Ren; Ding, Sai; Li, Pengyi; Han, Shiqing; Synlett; vol. 29; 2; (2018); p. 219 – 224;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 34270-90-1, 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 34270-90-1 as follows.

Example 7; difluorophenyl)-4-methyl-4-imorpholin-4-yl)cvclopentyl]methanone trifluoroacetate salt.; The product from Example 6 (17.2 mg, 0.027 mmol) in DMA (1 mL) was treated with cesium carbonate (63.3 rag, 0.194 mmol) and 2-iodoethyl ether (15.8 mg, 0.049 mmol) at rt. The mixture was heated at 1 0C for 16 h, then cooled to rt and filtered. The filtrate was directly purified by RP-HPLC (15 to 100% acetonitrile/water + 0.05% TFA) to afford the title compound. HPLC/MS: 601.4/603.4 (M+l); R 2.92 min (LC4).

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GRAHAM, Thomas, H.; LIU, Wensheng; SEBHAT, Iyassu, K.; SHEN, Dong-Ming; SHI, Zhi-Cai; WO2011/156220; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 450412-28-9, 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 450412-28-9 as follows.

Step 2. 6-bromo-2-chloro-3′-methyl-biphenyl: A 500-mL round-bottom flask under N2 atmosphere was charged sequentially with Pd(Ph3P)4, l-bromo-3-fluoro-2- iodobenzene (10 g, 0.032 mol) in toluene (80 mL), 2N aqueous sodium carbonate (55 mL) and 3-methylphenylboronic acid (5.16 g, 0.032mol) dissolved in ethanol (40 mL). This mixture was heated at reflux under N2 for 12 h and cooled to rt. The mixture was partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography to give 6-bromo-2-chloro-3′-methyl-biphenyl (6 g, 67%). 1H NMR (400MHz, CD3OD): 6.90-7.00 (t, 2H), 7.14-7.24 (m, 2H), 7.26- 7.33 (t, IH), 7.44-7.50 (d, IH), 7.58-7.62 (d, IH); MS (E/Z): 281 (M+H+)

According to the analysis of related databases, 450412-28-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124582; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com