Month: June 2021

Electric Literature of 460-37-7, 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 460-37-7 as follows.

A mixture of 109 3-ethyl-5-methylthieno-[2,3-d]pyrimidine-2,4(1H,3H)-dione (83) (2.0g, 9.51mmol) and 112 potassium carbonate (3.29g, 23.8mmol) in 45 DMF (50mL) was stirred for 15min at RT before 43 1,1,1-trifluoro-3-iodopropane (6.39g, 28.5mmol) was added. The reaction mixture was stirred at RT for 16h. Then the same amounts as before were added of 1,1,1-trifluoro-3-iodopropane and potassium carbonate, and stirring was continued at 50C. After 2h the conversion was complete. 113 Ethyl acetate was added to the cooled reaction mixture which was then successively washed with water (2 times) and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude was subjected to MPLC (Biotage Isolera, 340g silica cartridge, cyclohexane/ethyl acetate, 10:1). After evaporation of the solvent, 2.51g (85% yield) of the 114 title compound were obtained. 1H NMR (400MHz, DMSO-d6, delta/ppm): 6.88 (d, 1H), 4.12 (t, 2H), 3.91 (q, 2H), 2.78 (qt, 2H), 2.39 (d, 3H), 1.12 (t, 3H). 13C NMR (126MHz, DMSO-d6, delta/ppm): 157.90, 153.04, 149.47, 135.39, 126.19 (q), 113.23, 112.17, 41.51 (q), 35.68, 30.14 (q), 15.95, 12.68. LC/MS (method 2, ESIpos): Rt=1.90min, m/z=307.07 [M+H]+. HR-MS (ESIpos): m/z=307.0718 found, 307.0723 calculated [M+H]+. Mp: 104C.

According to the analysis of related databases, 460-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Haerter, Michael; Kalthof, Bernd; Delbeck, Martina; Lustig, Klemens; Gerisch, Michael; Schulz, Simone; Kast, Raimund; Meibom, Daniel; Lindner, Niels; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 763 – 778;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 689291-89-2, 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 689291-89-2 as follows.

To a stirred solution of 5-bromo-2-iodobenzaldehyde (4.2 g, 13.5 mmol, 1 .0 equiv) in THF (20 ml_) was added t-butyl amine (4.26 ml_, 40.6 mmol, 3.0 equiv) at room temperature, under nitrogen atmosphere. The reaction mixture was stirred for 40 h at room temperature and evaporated under vacuum to obtain a residue. The residue was dissolved in DCM (100 ml_) washed with H20 (50 ml_), dried over sodium sulphate and evaporated to obtain (£)-/V-(5-bromo-2-iodobenzylidene)-2-methylpropan-2-amine (3.0 g, crude) as a yellow oily compound. 1H NMR (400 MHz, CDCI3) delta ppm 1 .32 (s, 9H), 7.20 (dd, J=2.8, 8.4 Hz, 1 H), 7.68 (d, J=8.4 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H), 8.31 (s, 1 H).

According to the analysis of related databases, 689291-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 628-21-7, name is 1,4-Diiodobutane, 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 628-21-7, name: 1,4-Diiodobutane

Add in 250ml three-necked bottle19.4g anthrone (0.1mol),150ml dry THF, 1,4-diiodobutane (34.1g, 0.11mol) was added with stirringAnd 26.8g of potassium tert-butoxide (0.24mol), the reaction system was stirred at room temperature for 3 hours,The reaction was refluxed for another 3 hours. Add saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate,The liquid was dried and separated by column chromatography to obtain 13.6 g of white solid with a yield of 55%.

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

Reference:
Patent; Kunshan Weixinnuo Display Co., Ltd.; Tsinghua University; Beijing Weixinnuo Technology Co., Ltd.; Qiu Yong; Fan Hongtao; Duan Lian; (53 pag.)CN103172554; (2016); B;,
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. 16355-92-3, name is 1,10-Diiododecane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 16355-92-3

General procedure: N,N,N,N?,N?,N?-Hexabutylhexanediammonium diiodide (Bu6-diquat-6), N,N,N,N?,N?,N?-hexabutyloctanediammonium diiodide (Bu6-diquat-8), and N,N,N,N?,N?,N?-hexabutyldecanediammonium diiodide (Bu6-diquat-10) were synthesized by nucleophilic substitutionof the corresponding diiodoalkane with tributylamine. In a typical synthesis, to an oven-dried,nitrogen-filled, two-necked flask equipped with a condenser and a magnetic stirrer were addeddehydrated ethanol and tributylamine (3 equiv). Subsequently, diiodoalkane (1 equiv) was slowlyadded into the mixture. This mixture was heated slowly to 90 C and kept at this temperature in darkwhile stirring. After 48 h, the solution was cooled to room temperature and then ethanol wasevaporated by a rotary evaporator, producing semi-solid. This semi-solid was purified byrecrystallization in ethanol and ethyl acetate. The recrystallized solid was washed with acetone orhexane and dried under atmospheric condition.

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 16355-92-3.

Reference:
Article; Keoh, Sye Hoe; Chaikittisilp, Watcharop; Endo, Akira; Shimojima, Atsushi; Okubo, Tatsuya; Bulletin of the Chemical Society of Japan; vol. 90; 5; (2017); p. 586 – 594;,
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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,2-Dichloro-4-iodobenzene

a) (3,4-Dichloro-phenyl)-propynoic acid ethyl ester (Vb) Under argon atmosphere, a four neck flask was charged with 1,2-dichloro-4-iodo-benzene (222.8 g, 0.80 mol), bis(triphenylphosphine) palladium(II) chloride (11.2 g, 16.0 mmol, 2 mol %), copper(I) iodide (6.09 g, 32.0 mmol, 4 mol %) and dry THF (2.4 l). At r.t., cesium carbonate (526.6 g, 1.60 mol, 2 eq.) was added over 5 minutes. Afterward, propynoic acid ethyl ester (168.6 ml, 1.60 mol, 2 eq.) was added, and the reaction mixture was stirred overnight at 35 C. An additional portion of propynoic acid ethyl ester (17.0 ml, 0.16 mol, 0.2 eq.) was added, and the reaction was stirred for another 4 h at 35 C. The reaction mixture was evaporated to dryness, and the residue was taken up in toluene (0.8 l) and heptane (1.6 l). The resulting suspension was stirred at 40 C. for 1 h and filtered over celite. The filtrate was concentrated, and the product was purified by silica gel filtration (toluene/heptane 1:2) to yield 175.0 g (89%) of Vb as a white solid.

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; Hoffmann-Emery, Fabienne; Puentener, Kurt; Ratni, Hasane; US2010/152462; (2010); 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. 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 31599-60-7

General procedure: To a reaction tube containing (17alpha-20E)-21-(tri-n-butylstannyl)-19-norpregna-1,3,5(10)20-tetraene-3,17beta-diol, 2a, were added a few crystals of 2,6 di-tert-butyl-4-methylphenol and the substituted phenyl/xylyl iodide. The tube was dried under vacuum for 24 h, then exchanged with argon at least four times. Tetrakis(triphenylphosphine) palladium (0) (0.024 g, 0.02 mmol) and dried, degassed toluene (5 mL) were added and the reaction was heated at 110 C for 6-18 h. After cooling to room temperature, the reactuib mixture was transferred to a flask with ethyl acetate (50 mL), activated charcoal was added, the mixture heated to boiling, and then filtered through a Celite pad. To the filtrate containing the substituted phenyl vinyl estradiol derivative, fluorsil (4-8 g) was added and then mixture was evaporated to dryness. Hexane was then added to the slurry and the mixture was again evaporated to dryness. The substituted phenyl vinyl estradiol was isolated using flash chromatography and characterized by 1H and 13C NMR, elemental analysis

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 31599-60-7.

Reference:
Article; Hanson, Robert N.; McCaskill, Emmett; Tongcharoensirikul, Pakamas; Dilis, Robert; Labaree, David; Hochberg, Richard B.; Steroids; vol. 77; 5; (2012); p. 471 – 476;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 124700-41-0,Some common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, molecular formula is C7H4FIO2, 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.

Intermediate 1C: (3,4-Dihydroisoquinolin-2(lH)-yl)(2-fluoro-5-iodophenyl)methanone[00165] To a suspension of 2-fluoro-5-iodobenzoic acid (Aldrich, 5.27 g, 19.8 mmol) in CH2CI2 (35.0 mL) was added oxalyl chloride (14.9 mL, 29.7 mmol, 1M solution in CH2CI2) followed by 2 drops of DMF via syringe. Gas evolution was initiated and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was then quenched with sat. aq. NH4CI solution and extracted with EtOAc (3 x). The combined organic extracts were dried over Na2S04, filtered and concentrated in vacuo to give crude 2-fluoro-5-iodobenzoyl chloride which was used directly in the next step.[00166] The crude product obtained above was dissolved in CH2CI2 (49.6 mL) and cooled to 0 C. To the solution were added 1,2,3,4-tetrahydroisoquinoline (2.7 mL, 21.8 mmol) followed by 2,6-lutidine (4.6 mL, 39.7 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was washed IN HC1 (2 x) and the organic layer was extracted with CH2CI2 (2 x). The combined organic extracts were washed with sat. aq. NaCl solution and dried over a2S04. Filtration and concentration in vacuo provided the title compound (7.55 g, 95%) as a viscous, yellow oil. XH NMR (CDCI3, 1.5: 1 mixture of amide rotamers) delta 7.78-7.66 (m, 2H), 7.26-7.12 (m, 3.5H), 6.98- 6.86 (m, 1.5H), 4.92 (s, 1.5H), 4.50 (br s, 0.5H), 3.65-3.52 (m, 1.5H), 3.04-2.95 (m, 1H), 2.92-2.82 (m, 1.5H); MS(ESI+) m/z 382.1 (M+H)+.

The synthetic route of 124700-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; CAI, Zhen-wei; TEBBEN, Andrew J.; PEREZ, Heidi L.; ZHANG, Liping; SCHROEDER, Gretchen M.; WEI, Donna D.; WO2012/162365; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 98-61-3, name is 4-Iodobenzenesulfonyl chloride, 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 98-61-3, Recommanded Product: 4-Iodobenzenesulfonyl chloride

A mixture of 4-Iodo-benzenesulfonyl chloride (302 mg, 1.0 mmol), mesitylene (120 mg, 1.0 mmol) and AICI3 (150 mg, 1.2 mmol) in DCM (5 mL) was stirred for 2 hours at room temperature. The mixture was then poured into 10 mL of 5% HCl (aq.), and extracted by DCM (30 mL). The organic phase was washed by aqueous KHCO3, brine, and dried over anhydrous Na2SC>4. The resulting solution was evaporated, and the residue was purified by silica gel column chromatography (Hexane/EtOAc = 10/1) to give the desired product as a white solid (266 mg, 69%). H NMR (600 MHz, CDCI3) delta 7.82 (d, 2H, J= 7.8 Hz), 7.48 (d, 2H, J= 7.8 Hz), 6.94 (s, 2H), 2.57 (s, 6H), 2.30 (s, 3H).

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

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHENG, Xiaodong; ZHOU, Jia; TSALKOVA, Tamara; MEI, Fang; CHEN, Haijun; WO2013/119931; (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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-amino-5-iodobenzoate

EXAMPLE 1002-(4-((2-Chlorothiophene-5-carboxamido)methyl)-lH-l,2,3-triazol-l-yl)-5-(2-oxopyridin- l(2H)-yl)benzoic acid (100); SCHEME 9Step 1 : Methyl 2-amino-5-iodonezoate (3.00 g, 10.8 mmol) was stirred in 35 rnL TFA in ice bath. To it was added sodium nitrite (820 mg, 12 mmol) in small portions. The mixture was stirred in ice bath for 40 min. To it was added an ice-cold solution of sodium azide (1.41 g, 21.6 mmol) in 8 mL water. The mixture was stirred for 3 hrs, diluted with ethyl acetate (500 mL), washed with brine three times, dried, and concentrated in vacuo to give compound 9.2 in quantitative yield.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. Product Details of 624-75-9

A mixture of [4- (4-HYDROXYPHENYL) butyl] carbamic acid tert-butyl ester 31 (0.365 g, 1.37 mmol) and Cs2CO3 (0.672 g, 2.06 mmol) in anhydrous DMF (8 mL) was heated at 65 C for 30 min. IODOACETONITRILE (0.276 g, 1.651 mmol) was then added to the mixture in one portion. The mixture was stirred at 65 C overnight, and then cooled to room temperature. The precipitated solid was filtered, and the filtrate was partitioned between water and dichloromethane (each 50 mL). The organic layer was separated, washed with brine (3 x 50 mL), dried over anhydrous NA2S04 and concentrated under vacuum. The residue was chromatographed on silica gel, eluting with a mixture of diethyl ether/dichloromethane (6: 94, v/v), to afford the desired product 40 (0.109 g, 38% yield) as a colorless viscous OIL. 1H NMR (300 MHz, CDC13) : 8 1.43 (s, 9H), 1.57 (M, 4H), 2.60 (t, 2H), 3.15 (M, 2H), 4.49 (br, 1H), 4.75 (s, 2H), 6.91 (d, 2H), 7.13 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; PARION SCIENCES, INC.; WO2005/18644; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com