Month: June 2021

Some common heterocyclic compound, 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, molecular formula is C4H8I2O, 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. Application In Synthesis of 1-Iodo-2-(2-iodoethoxy)ethane

Potassium carbonate (304 mg, 2.2 mmol) was added to a solution of 3b (76 mg, 0.22 mmol) and 2-iodoethyl ether (33 mg, 0.1 mmol) in MeCN (5 mL) and the mixture was stirred at reflux for 3 days. The reaction mixture was cooled, poured into water (50 mL) and the product extracted into CH2Cl2 (3×20 mL). The combined organic layer was washed with brine (15 mL), dried (Na2SO4), and the solvent removed in vacuo. The crude product was purified by radial chromatography (EtOAc/hexane=1:4-1:1) to give 10 (0.039 g, 51.3%) as a 1:1 mixture of diastereomers; white solid; IR (KBr) 2930, 2876, 1663 cm-1; 1H NMR (200 MHz, CDCl3) delta 7.96-7.76 (m, 4H), 7.72-7.29 (m, 16H), 5.07-4.83 (m, 4H), 3.55-3.19 (m, 8H), 2.72-2.48 (m, 2H), 2.48-2.27 (m, 2H), 2.26-1.94 (m, 4H), 1.94-1.66 (m, 4H); 13C NMR (50 MHz, CDCl3) delta 162.0, 136.3, 135.1, 134.0, 131.0, 129.7, 128.8, 128.7, 128.5, 76.7, 75.9, 72.0, 71.7, 66.4, 66.3, 50.6, 33.9, 25.9, 20.3. Anal. Calcd for C40H44N2O9S2·H2O: C, 61.68; H, 5.95; N, 3.60. Found: C, 61.47; H, 5.90; N, 3.31.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34270-90-1, its application will become more common.

Reference:
Article; Liu, Yuan; Jacobs, Hollie K.; Gopalan, Aravamudan S.; Tetrahedron; vol. 67; 12; (2011); p. 2206 – 2214;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

618-91-7, name is Methyl 3-iodobenzoate, 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. Safety of Methyl 3-iodobenzoate

General procedure: In a 10 mL glass screw cap tube capped with a rubber septum, palladium acetate Pd(OAc)2, (5 mg, 0.023 mmol), 1,3-bis(diphenylphosphino)propane dppp, (9 mg, 0.023 mmol) were introduced under argon atmosphere. Then, 3 mL of freshly distilled toluene) were added under argon. The mixture was stirred for 10 min to allow formation of the catalyst. Then securinine 1 (100 mg, 0.46 mmol), potassium carbonate (K2CO3, 127 mg, 0.92 mmol) and the desired iodoarene (0.92 mmol) were added. The septum was replaced by a screw cap, and the mixture was stirred at 130 C, in an oil bath. After 24 h stirring, the reaction mixture was brought to room temperature and diluted with ethyl acetate (5 mL). The reaction mixture was filtered through a pad of Celite eluting with AcOEt (20 mL). The organic layer was extracted with a saturated aqueous solution of sodium hydrogen carbonate (10 mL) and brine (10 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification by flash column chromatography on silica gel (pentane-ethyl acetate) affords the desired coupling product. 4.1.2.1.14 Methyl 3-((6S,11aR,11bS)-2-oxo-2,6,9,10,11,11a-hexahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-5-yl)benzoate(2n) Yield: 67%. Orange solid; m.p. 54-56 C; Rf 0.32 (petroleum ether-AcOEt, 70:30); [alpha]D20 – 505 (c = 0.11, CHCl3); 1H NMR (300 MHz, CDCl3): delta = 8.18 (s, 1H), 8.02 (d, J = 7.8 Hz, 1H), 7.69 (d, J = 7.8 Hz, 1H), 7.48 (dd, J = 7.8 Hz, 1H), 6.86 (d, J = 1.3 Hz, 1H), 5.61 (s, 1H), 4.38 (d, J = 4.2 Hz, 1H), 3.92 (s, 3H), 2.92-2.86 (m, 1H), 2.64 (dd, J = 9.3, 4.2 Hz, 1H), 2.33-2.18 (m, 2H), 1.91-1.82 (m, 2H), 1.68-1.47 (m, 4H), 1.26-1.14 (m, 1H); 13C NMR (75 MHz, CDCl3): delta = 173.6, 169.9, 166.3, 149.1, 138.7, 130.9, 130.4, 130.2, 129.0, 127.4, 116.2, 105.2, 89.0, 63.0, 61.6, 52.3, 48.8, 41.9, 27.4, 25.8, 24.1. MS (CI, NH3): m/z = 352 [M+ + H]. HRMS calcd for C21H21N O4H [M+ + H]: 352.15433; found: 352.15386, error = 1.3 ppm.

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perez, Marc; Ayad, Tahar; Maillos, Philippe; Poughon, Valerie; Fahy, Jacques; Ratovelomanana-Vidal, Virginie; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 287 – 293;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 627-32-7, name is 3-Iodo-1-propanol, 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 627-32-7, HPLC of Formula: C3H7IO

EXAMPLE 1Preparation of (9Z,i7E)-3-(nitrooxy)propyl octadeca-9,ll-dienoate (9Z, 11 E)-3-(nittauooxy)ptauopy octadeca-9,11-dienoate was synthesised in accordance with the procedure set out below:(A) To a solution of silver nitrate (5.34 g, 31.11 mmol) in acetonitrile (100 ml) was added dropwise via syringe 3-iodo-propan-l-ol (2.6 ml, 4.90 g, 26.33 mmol). The reaction mixture was stirred at room temperature for 48 h, then filtered over Celite. The filtrate was concentrated under reduced pressure and the residual oil was purified by flash chromatography (Petroleum Ether / EtOAc 7:3) yielding 3-hydroxypropyl nitrate as a brown oil (3.02 g, 24.95 mmol, 94 %), as shown below:AgNO3O2N(XMeCNRf 0.20 (Pet. Ether / EtOAc 7:3)Bp 56-58 C / 0.15 Torr (lit.)1H NMR 1.96 (p, 2H, J=6.2 Hz, CH2), 2.06 (s, IH, OH), 3.74 (dt, IH, J=2.2,6.1 Hz, CH2O), 4.59 (t, IH, 7=5.3 Hz, CH2ONO2)13C NMR 29.5 (CH2), 58.6 (CH2O), 70.2 (CH2ONO2) IR 1283, 1634, 3368Mass 122 (M+ 1, 10 %), 104 (16 %), 75 (17 %), 59 (27 %), 46 (100 %)

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; UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND; WO2009/127398; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, name is 3-Iodo-4-methylbenzoic 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. Application In Synthesis of 3-Iodo-4-methylbenzoic acid

3-Iodo-4-methylbenzoic acid (2.0 g, 7.6 irunol) was taken up in SOCl2 (4 mL) . The resulting slurry was allowed to reflux for 2h upon which time the reaction was concentrated under reduced pressure to afford the corresponding acid chloride, which was used without further purification. The off white acid-chloride solid was taken up in CH2Cl2 (70 mL) followed by the addition of DIEA (1.5 mL, 8.4 mmol) and 3- (trifluoromethyl)aniline (0.86 mL, 6.9 mmol) . The mixture was allowed to stir at room temperature for 3 h. The reaction mixture was diluted with CH2Cl2 (70 mL) and washed with aq. HCl (IM, 25 mL) , sat. aq. NaHCO3 (25 mL) , brine (25 mL) , dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 3-iodo-4-methyl-N- (3- (trifluoromethyl)phenyl)benzamide as an off white solid. MS m/z = 406 [M+H]+. CaIc’d for C15H11F3INO: 405; Step 4: N-cyclopropyl-3-iodo-4-methylbenzamide To 3-iodo-4-methylbenzoic acid (3.5 g, 13 mmol) was added thionyl chloride (10 mL) before heating the mixture to reflux for 1.5 h. The reaction mixture was concentrated in vacuo, and dissolved in DCM (50 mL) and Hnigs base (4.6 mL, 27 mmol). After the addition of eyelopropylamine (1.87 mL, 27 mmol) at -78 0C, the reaction mixture was stirred at ambient Temp, for about 3 h. The mixture was diluted with 100 mL DCM, washed with 20 mL saturated, aqueous. NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4. The solid EPO obtained was suspended in EtOAc and filtered to give the title compound. MS (ES+) : 302 (M+H)+; 3-iodo-4-methylbenzoyl acid chlorideInto a 100 mL round bottom flask is placed -3-iodo-4- methyl benzoic acid (10 g, 38.175 mmol) and thionyl chloride (25 mL, 344 mmol) . The reaction was allowed to stir at reflux for 2 hours. The reaction was cooled to room temperature and concentrated under reduced pressure. The EPO concentrate was placed under high vacuum for about 24hr and afforded the title acid chloride as a light yellow solid.

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 3718-88-5, 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. 3718-88-5 name is 3-Iodobenzylamine hydrochloride, 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.

Recrystallization from H2 O-EtOH provided m-iodobenzylguanidine sulfate as colorless crystals: mp 166-167 C.; HPLC [THF/0.1M NaH2 PO4 12/88, 3.0 ml/min] showed only one peak tR= 8.6 min; IR (nujol) 3340 (NH), 3160 (NH), 1660 and 1630 (C=N), 1090 (S=0), 780 and 695 cm (1,3-disubstituted benzene); PMR (CD3 OD) delta4.36 (S,2,CH2), 6.96-7.73 [m(7 peaks), 4,arom]; the aromatic peak pattern was identical to that observed for m-iodobenzylamine hydrochloride in CD3 OD. Anal. Calcd for C8 H10 IN3.O.5H2 SO4: C,29.64; H, 3.42. Found C,29.55,H, 3.40.

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

Reference:
Patent; Wieland; Donald M.; Brown; Lawrence E.; Beierwaltes; William H.; Wu; Jiann-long; US4584187; (1986); 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. 69113-59-3, name is 3-Iodobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H4IN

EXAMPLE 18.1 (+-)-3-{(6R,9aS)-[(3-chlorophenyl)ethynyl]octahydro-2H-pyrido[1,2-a]pyrazin-2-yl}pyrazine-2-carbonitrile Bis(triphenylphosphine)palladium(II) dichloride (0.018 mmol) and copper(I) iodide (0.03 mmol) were added to a microwave vial with a stir bar. 3-iodobenzonitrile (0.45 mmol) and (+-)-3-[(6R,9aS)-6-ethynyloctahydro-2H-pyrido[1,2-a]pyrazin-2-yl]pyrazine-2-carbonitrile (0.3 mmol, 80.2 mg) was dissolved in THF (1 mL) and added to the microwave vial with stirring, followed by Et3N (1 mL). The vial was sealed and microwaved at 90 C for 6 min. The resulting mixture was then diluted with DCM and washed with water. The organic phase was purified by column chromatography to yield the desired product (80.3 mg, 73%). 1H NMR 300 MHz, (CDCl3) delta (ppm): 1.41 (m, 2H); 1.72 (m, 1H); 1.87 (m, 2H); 2.12 (m, 1H); 2.21 (m, 1H); 2.31 (td, 1H); 2.95 (dd, 1H); 3.09 (dd, 1H); 3.33 (td, 1H); 3.69 (d, 1H); 4.35 (d, 1H); 4.51 (d, 1H); 7.43 (t, 1H); 7.58 (d, 1H); 7.64 (d, 1H); 7.69 (s, 1H); 8.00 (d, 1H); 8.25 (d, 1H).

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; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/37817; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 25309-64-2, These common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-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.

General procedure: Rh(cod)2BF4(6 mol%), DPPP (0.09 mmol), Na2CO3 (1 mmol) and 4A MS (SiO2,powder, 150 mg) were transferred into an oven-dried tube (15 mL), which was evacuated and backfilled with N2 (5x). 2-Methyltetrahydrofuran (2.5 mL), alkyl or aryl iodide (1 mmol),HMF (1.2 mmol) were added into the tube via syringe and sealed with Teflon plug. The reaction mixture was stirred at 125 C for24 h. After the reaction was complete, the mixture was concentrated by rotary evaporation. The crude product was purified by column chromatography (EA/PE = 1/20) on a silica gel to afford the desired product.

Statistics shows that 1-Ethyl-4-iodobenzene is playing an increasingly important role. we look forward to future research findings about 25309-64-2.

Reference:
Article; Qi, Xinxin; Zhou, Rong; Ai, Han-Jun; Wu, Xiao-Feng; Journal of Catalysis; vol. 381; (2020); p. 215 – 221;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

170112-66-0, name is 3,4,5-Trifluoroiodobenzene, 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. Formula: C6H2F3I

General procedure: Arene (0.10 mmol, 1.0 equiv), Pd(OAc)2 (2.2 mg, 10 mumol,10 mol%), ligand (15 mol% or 20 mol%), hydrogen phosphate (15 mol% for benzylamine substrate), aryl iodide (0.3 mmol, 3.0 equiv.) and silver acetate (50 mg, 0.30 mmol, 3.0 equiv.) were added into a 2-dram reaction vial. Solvent and (+)-NBE-CO2Me (20 mol% or 50 mol%) were added to the mixture. The vial was flushed with N2 and capped. The reaction mixture was then stirred at the selected temperature for 12-24 h. After cooling to room temperature, the mixture was filtered through Celite and eluted with ethyl acetate. The filtrate was evaporated under reduced pressure. Purification by preparative thin-layer chromatography afforded the desired product.

The synthetic route of 170112-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Hang; Herron, Alastair N.; Shao, Ying; Shao, Qian; Yu, Jin-Quan; Nature; vol. 558; 7711; (2018); p. 581 – 585;,
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 19094-56-5 as follows. Safety of 2-Chloro-5-iodobenzoic acid

5-iodoaniline-2-chlorobnenzoic acid 3. 3g soln. ethanol 150 ml, concentrated hydrochloric acid 0. 11g is added, heated under reflux for 12 hours. After returning the reaction solution to room temperature, is diluted with water, adding an aqueous solution of sodium hydroxide 1N, 3 times extracted with ethyl acetate. The organic layer, washed with saturated saline solution, dried with magnesium sulfate waterlessly org. layer. By concentrating the pressure somas, 5-iodoaniline-2-ethyl chlorobnenzoic (43) 1. 74g is obtained.

According to the analysis of related databases, 19094-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OAT AGRIO COMPANY LIMITED; UENAKA, GO; MASUMOTO, SATORU; HAYASHI, NAOTAKA; (63 pag.)JP5743418; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 19094-56-5, 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. 19094-56-5, name is 2-Chloro-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2-chloro-5-iodo-benzoic acid (25.63 g, 90 mmol) in methanol (500 ML) saturated with HCL gas was stirred at room temperature for 48H. The reaction mixture was concentrated I71 vacuo, diluted with 1: 1 ethyl ACETATE/DIETHYL ether and washed with saturated aqueous sodium bicarbonate and brine. The organiclayer was dried over sodium sulfate, filtered and concentrated ILL vacuo to afford the title compound (25.0 g).

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/99146; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com