Month: June 2021

Related Products of 19099-54-8, These common heterocyclic compound, 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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: Catalyst 2c (prepared according Ref. 26b, 133 mg, 6.2 equiv of Pd) was added to a solution of aryl iodide (0.20 mmol, 1.0 m equiv), alkene (0.40 mmol, 2.0 equiv) in DMF (2 mL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, compound 2c was filtered off under vacuum using a 0.2 mum membrane. The mixture of solvents was concentrated under vacuum to afford pure 3a-j after drying under vacuum (0.1 mbar). The catalyst 2c was then regenerated by reaction with NBu3 (0.16 mL, 0.66 mmol, 3.3 equiv) in DMF at rt for 3 h. Compound 2c was then filtered under vacuum, washed with Et2O (2 mL), and dried under vacuum.

The synthetic route of 19099-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Derible, Antoine; Yang, Yun-Chin; Toy, Patrick H.; Becht, Jean-Michel; Le Drian, Claude; Tetrahedron Letters; vol. 55; 31; (2014); p. 4331 – 4333;,
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. 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-Iodo-2-(2-iodoethoxy)ethane

INTERMEDIATE 18(2-Oxo-2′.3′.5′.6′-tetrahvdrospirorindole-3.4′-Pyran1-l(2H)-vnacetic acidStep A. 2′.3′.5′.6′-Tetrahvdrospirorindole-3.4′-pyran1-2?/f)-oneButyllithium (2.5 M in hexanes, 3.76 mL, 9.39 mmol) was added to a solution of oxindole (500 mg, 3.76 mmol) at -78 0C in THF (40 mL). After complete addition, NJIJt’.N’- tetramethylethane-l,2-diamine (1.48 mL, 9.76 mmol) was added, maintaining the internal temperature < -70 C. After 1 h at -78 C, 2-iodoethyl ether (4.90 g, 15.0 mmol) was added and the reaction warmed to ambient temperature. After 48 h the reaction was quenched with H2O (5 mL) and the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous solution was extracted with EtOAc (3 chi 50 mL) and the combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient Of CH2Cl2MeOH - 100:0 to 97:3, gave the title compound. MS: m/z = 204 (M + 1). The synthetic route of 34270-90-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK & CO., INC.; WO2008/130512; (2008); 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. 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,2-Dichloro-3-iodobenzene

H. 17alpha-Chloro-17beta-(2′-Methylbenzylsulfinyl)-1,4-Androstadiene-3,11-Dione In a manner similar to that described in Example 2A, react 0.946 gm. of 17alpha-(2′-methylbenzylthio)-1,4-androstadiene-3,11-dione, 32 ml. of pyridine, 8 ml. of water and 1.6 gm. of iodobenzene dichloride. Slurry the residue with ethyl acetate/ether and filter to obtain the title compound; [alpha]D26 +135° (CHCl3); lambdamaxMeOH 228 nm (epsilon=22,000).

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 2401-21-0.

Reference:
Patent; Schering Corporation; US4183924; (1980); A;,
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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3-iodo-4-methylbenzoate

A suspension of Example 191A (2.32 g, 6.62 mmol), methyl 3-iodo-4-methylbenzoate (1.83 g, 6.62 mmol), cesium fluoride (2.01 g, 13.25 mmol) and [(i-butyl)2PCl]2PdCl2 (PXPd, 108 mg, 0.20 mmol) in AyV-dimethylformamide (33 mL) was warmed at 90C for 18 hours. The mixture was cooled and diluted with ethyl acetate and extracted with water (3x) and saturated sodium chloride solution. The solution was dried ( a2S04), filtered, and stirred with 3-(mercaptopropyl) silica gel for 1 hour. Concentration in vacuo afforded a brown oil, which was chromatographed over a 220 g silica gel cartridge, eluting with 10-60% ethyl acetate in hexanes. The solid obtained was triturated with ether-hexanes and collected by filtration. After drying in a vacuum oven at 50 C for 18 hours, these procedures afforded the title compound (1.43 g, 58%>) as white solid. MS (ESI+) m/z (rel abundance) 373 (100, M+H)+, 374 (23).

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, 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. COA of Formula: C9H9IO3

General procedure: 3-Iodo-4,5-dimethoxybenzaldehyde (1.5 mmol) and 2,4-dimethyl-3-ethylpyrrole (3.3 mmol) were dissolved in absolute CH2Cl2 (30 mL) under N2 atmosphere, 10 drops of TFA were added and the solution was stirred at rt overnight or until TLC analysis showed complete consumption of the aldehyde. At this time of DDQ (2.5 mmol) were added and stirring continued for 20 min. Then, Et3N (4 mL) and BF3·OEt2 (4 mL) were added. The mixture was stirred for 12 h then the organic layer containing the crude product was subsequently washed three times with water; the organic solution was dried over Na2SO4, and evaporated to dryness. The raw material was chromatographed (SiO2, petroleum ether/CH2Cl2, 6:4) affording 280 mg (yield: 33%) of 1a in the form of orange needles

The synthetic route of 32024-15-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Banfi, Stefano; Nasini, Gianluca; Zaza, Stefano; Caruso, Enrico; Tetrahedron; vol. 69; 24; (2013); p. 4845 – 4856;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1829-28-3, A common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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 dry and argon-flushed Schlenk tube, equipped with a magnetic stirring bar and a rubber septum was charged with Ni(acac)2 (12.8 mg, 0.05 mmol, 0.05 equiv) as catalyst, 4-fluorostyrene (24.4 mg, 0.20 mmol, 0.20 equiv), the aryl iodide or heteroaryl chloride 3 as electrophile (1.00 mmol, 1.00 equiv), and freshly distilled THF (1 mL). The resulting suspension was cooled to 0 °C and the prior prepared benzylic manganese chloride solution (1.20 mmol, 1.20 equiv) was added dropwise at the prior adjusted temperature. The reaction conversion was monitored by GC analysis of hydrolyzed aliquots. After full conversion of the selected electrophile, the reaction mixture was quenched with a sat. aq NH4Cl and extracted with EtOAc (3 × 75 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification of the crude product by flash column chromatography afforded the desired products.

The synthetic route of 1829-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Benischke, Andreas D.; Desaintjean, Alexandre; Juli, Thomas; Cahiez, Gerard; Knochel, Paul; Synthesis; vol. 49; 24; (2017); p. 5396 – 5412;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 7425-53-8, 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. 7425-53-8, name is Ethyl 4-iodobutanoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 100 ml round bottom flask, ethyl4-bromobutyrate (6.0 ml, 40.2 mmol: 1H NMR (300 MHz, CDCl3) delta 4.14(q, J = 7.2 Hz, 2H), 3.47 (t, J = 6.5 Hz, 2H), 2.49 (t, J = 7.2 Hz, 2H), 2.17(m, 2H), 1.26 (t, J = 7.1 Hz, 3H).) was dissolved in 40 ml acetone. Potassium iodide (13.35 g, 80.4 mmol,2.0 equiv.) was added, a reflux condenser was attached, and the reaction was heated at reflux for 12h. Thesolution was cooled, filtered through a course fritted funnel, and concentrated in vacuo. The resultingyellow oil with fine particulates was taken up in ca 50 ml of 1:1 Hex:Et2O and filtered through neutralaluminum to remove color. After flushing with an additional 100 ml 1:1 Hex:Et2O, the solution wasconcentrated to yield 8.44 g (87%) of ethyl 4-iodobutyrate 12. 1H NMR (300 MHz, CDCl3) delta 4.14 (q, J =7.2 Hz, 2H), 3.24 (t, J = 6.8 Hz, 2H), 2.44 (t, J = 7.1 Hz, 2H), 2.13 (m, 2H), 1.26 (t, J = 7.2 Hz, 3H). A 50ml Schlenk flask was flame dried under vacuum, cooled to 23 C, and charged with ethyl 4-iodobutyrate (8.4 g, 34.7 mmol) and copper(I) iodide (10 mg, 0.05 mmol). After sealing with a greased ground glass stopper, the flask was evacuated and refilled with Ar. The stopper was replaced with a rubber septum andneat diethyl zinc (14 ml, 137 mmol, 4 equiv) was added via syringe. The reaction was heated at 40 C for12 h. The excess diethyl zinc and ethyl iodide were removed under vacuum for 2 h into a trap withmethanol cooled to -78 C with dry ice and acetone. (CAUTION: A trap cooled with liquid nitrogeneasily clogs so dry ice/acetone cooling is preferred. Methanol quenches the excess diethyl zinc, but careshould be taken when cleaning the trap as some diethyl zinc may remain.) After backfilling with Ar, THF (5 ml) was added to the reaction vessel and heated at 40 C for 1 h under Ar. The reaction vessel wasevacuated for 1 h. This step was repeated another two times. After cooling to 23 C, the generated bis(4-ethoxy-4-oxobutyl)zinc was diluted with 15 ml of THF and this solution was used directly in the desymmetrization reaction.

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 4-iodobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Oberg, Kevin M.; Cochran, Brian M.; Cook, Matthew J.; Rovis, Tomislav; Synthesis; vol. 50; 22; (2018); p. 4343 – 4350;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Methyl 2-amino-5-(phenethylthio)benzoate (2) Synthesized using reported procedure with modification (see, e.g., Itoh, T; Mase, T. Org. Lett. 2004, 6, 4587-4590). To a round-bottom-flask under nitrogen were added methyl 2- amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), z-P^Net (775 mg, 1.05 mL, 6 mmol, 2.0 equiv.) and dry 1,4-dioxane (30 mL). Catalyst Pd2(dba)3 (137 mg, 0.15 mmol, 0.05 equiv.), Xantphos (173 mg, 0.3 mmol, 0.1 equiv.) were then added and the mixture were stirred for 15 minutes. 2-Phenylethanethiol (415 mg, 0.4 mL, 3 mmol, 1.0 equiv.) was added and then the mixture was heated to reflux for 16 hours. The reaction mixture was then allowed to cool down to room temperature. The reaction mixture was then filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=15:85) on silica gel to afford 2 (862 mg, 82%) as yellow oil which solidified upon standing. XH NMR (300 MHz, CDC13) delta 7.99 (s, 1H), 7.37-7.14 (m, 6H), 6.62 (d, J= 6.0 Hz, 1H), 5.80 (s, 2H), 3.87 (s, 3H), 3.04-2.99 (m, 2H), 2.87-2.82 (m, 2H); 1 C NMR (75 MHz, CDC13) delta 168.01, 149.86, 140.36, 138.81, 135.95, 128.50, 128.41, 126.28, 120.81, 117.42, 111.11, 51.64, 37.81, 35.94.

The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 204257-72-7,Some common heterocyclic compound, 204257-72-7, name is Methyl 2-fluoro-4-iodobenzoate, molecular formula is C8H6FIO2, 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.

In a round-bottomed flask chiral(2S,3R,4S,5R)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-2-(2,2-dimethyl-propyl)-5-hydroxymethyl-1-prop-2-ynyl-pyrrolidine-3-carbonitrile (30 mg, 61.1 mumol), methyl 2-fluoro-4-iodobenzoate (17.1 mg, 61.1 mumol, Eq: 1.00) were dissolved in toluene (1.2 ml) then cuprous iodide (2.33 mg, 12.2 mumol) dichlorobis(triphenylphosphine) palladium (II) (1.29 mg, 1.83 mumol) and triethylamine (6.16 mg, 8.51 mumol, 61.1 mumol) were added and stirred under nitrogen atmosphere at 25 C. for 16 hours (protect from light with aluminum foil around flask during reaction conditions). Work up by filtration through celite, wash with EtOAc, mixture concentrated under reduced vacuum to yield a crude oil. Purification by RP-HPLC (40-95% acetonitrile/water) to afford chiral methyl 4-(3-((2S,3R,4S,5R)-4-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-5-(hydroxymethyl)-2-neopentylpyrrolidin-1-yl)prop-1-ynyl)-2-fluorobenzoate (17.3 mg, 26.9 mumol, 44.0% yield) as an off-white foam. HRMS (ES+) m/z Calc for C26H26Cl2F2N2O+H[(M+)1+]: calc: 643.1737. found: 643.1735.

The synthetic route of 204257-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Jin-Jun; Ross, Tina Morgan; US2012/149660; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 31599-61-8, 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. 31599-61-8 name is 4-Iodo-1,2-dimethylbenzene, 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: Amide derivatives (0.2 mmol), 4-methoxy iodobenzene (3 equiv.), Pd(OAc)2 (10 mmol%), C6H13COOAg (2 equiv.) were combined in o-xylene (1 mL) in a 10mL vial. The vial was sealed with a Teflon lined cap, and the reaction was stirred in 120 C oil bath for 24 hours without an inert gas atmosphere. After cooled to room temperature, the mixture was extracted with ethyl acetate (3 x 10mL). The residue was purified by silica-gel column chromatography to afford the corresponding product.

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

Reference:
Article; Yan, Xufei; Long, Rongrong; Luo, Feihua; Yang, Li; Zhou, Xiangge; Tetrahedron Letters; vol. 58; 1; (2017); p. 54 – 58;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com