Category: iodides-buliding-blocks

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. 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Iodo-3,5-bis(trifluoromethyl)benzene

Step K: Synthesis of ethyl 3,5-bis(trifluoromethyl)phenylphosphinate AZ3. To a degassed solution of 1-iodo-3,5-bistrifluoromethylbenzene (10.0 g, 29.4 mmol), anilinium hypophosphite (5.62 g, 35.3 mmol) and 3-aminopropyl triethoxysilane (7.81 g, 35.3 mmol) in anhydrous acetonitrile (200 mL) were added palladium acetate (132 mg, 0.588 mmol, 2 mol percent) and 1,3-bis(diphenylphosphino)propane (267 mg, 0.647 mol, 2.2 mol percent). The mixture was heated under reflux overnight, then cooled down to room temperature, diluted with ethyl acetate and hydrochloric acid (1 M), and partitioned. The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine, and dried over sodium sulfate. The volatiles were removed in vacuo, and the residue was purified by column chromatography using 30 to 70percent ethyl acetate in petroleum ether to afford compound AZ3 (4.65 g) as a cloudy oil in 52percent yield. 1H NMR (CDCl3, 400 MHz): delta 1.45 (t, J=7.1 Hz, 3H), 4.18-4.35 (m, 2H), 7.69 (d, J=579.6 Hz, 1H), 8.10 (s, 1H), 8.23 (s, 1H), 8.27 (s, 1H). 31P NMR (CDCl3, 161.8 MHz): delta 19.59 (J=580.6 Hz).

The synthetic route of 328-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2009/202480; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 90347-66-3, 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 90347-66-3 as follows.

A dry flask was charged with 3-iodo-4-methylbenzoic acid methyl ester (21.6 G, 78. 2 MMOL) and the flask was evaporated and then filled with argon and this process repeated twice. Dry THF (140 mL) was added, and the solution cooled to-50 C ; then isopropyl magnesium chloride (41 mL, 2.0 M in diethyl ether, 82 MMOL) was added slowly over 15 min keeping the temperature below-40 C. On completion of the addition the reaction mixture was stirred at-40 C for 45 min. A THF solution of ZnCl2 (10.78 G, 79.1 MMOL, 0.8 M) was added dropwise over 20 min. The reaction mixture was stirred at 0 C for 65 min; then 2-chloro-4-nitro-benzoyl chloride (17. 2 g, 78.2 MMOL) and TETRAKIS (TRIPHENYLPHOSPHINE) PALLADIUM (0) (4.03 g, 3. 49 MMOL) were added and the reaction mixture was allowed to warm to room temperature. After 4 h the reaction mixture was poured into a mixture of toluene/EtOAc/water, then shaken and separated. The aqueous phase was extracted with two more portions of EtOAc. The organic phases were combined, dried (MGS04), filtered, and concentrated in vacuo to afford the crude product. Crystallization from mixtures of ETOAC/PETROLEUM ether (40- 60) gave the title compound as yellow solid. The mother liquid was concentrated in vacuo and purified by chromatography using DCM as the eluent to give a second crop of the title compound.

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; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 2043-55-2, These common heterocyclic compound, 2043-55-2, name is 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane, 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.

Diethyl malonate (11.5 mL, 75.7 mmol) was added dropwise to an ice-cold suspension of sodium hydride (60percent dispersion in mineral oil, 2.21 g, 55.4 mmol) in THF (150 mL) at 0 °C during 15 min. The resulting mixture was stirred for 30 min while allowing the temperature from 0?23 °C. 1H,1H,2H,2H-nonafluorohexyl iodide (9.4 mL, 50.5 mmol) was added slowly to the reaction and the mixture was heated at reflux for 3 h, and then was cooled to 23 °C. Water (100 mL) and ethyl ether (100 mL)were added to it. The aqueous layer was extracted with ethyl ether (3 80 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography to afford diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (6) as a colorless liquid (18.2 g, 89 percent). 1H NMR (400 MHz, CDCl3): delta 4.30?4.17 (m, 4H), 3.44?3.40 (m, 1H), 2.23?2.13 (m, 4H), 1.30?1.26 (m, 6H). 19F NMR (CDCl3, 376 MHz): delta -81.98 (3F, tt, J1 = 11.2 Hz, J2 = 3.7 Hz), 115.37 (2F, quintet, J = 15.0 Hz), 125.33 to 125.36 (2F, m), 126.89 to 126.96 (2F, m). 13C NMR (100 MHz, CDCl3): delta 168.61, 61.90, 50.77, 28.46, 19.77, 14.06; ESI-MS (m/z): 429 [M+Na]+. Anal. Calcd. for C13H15F9O4: C, 38.44; H, 3.72. Found: C, 38.12; H, 3.87.

The synthetic route of 2043-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bodduri, V.D. Vijaykumar; Chirumarry, Sridhar; Lim, Jae-Min; Lee, Yong-Ill; Jang, Kiwan; Choi, Bong-In; Chung, Seon-Yong; Shin, Dong-Soo; Journal of Fluorine Chemistry; vol. 163; (2014); p. 42 – 45;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, 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 21740-00-1, Recommanded Product: 21740-00-1

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 × 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
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 89459-38-1 as follows. Application In Synthesis of 2-Iodo-4-nitrobenzoic acid

A mixture of Example 2.140.1 (130 g) in a mixture of methanol (1000 mL) and sulfuric acid (23.65 mL) was stirred at 85 C. for 16 hours and concentrated to dryness. The residue was triturated with methanol (100 mL) and the suspension was stirred for 10 minutes. The solid was collected by filtration, washed with water (200 mL*3) and methanol (20 mL), and air-dried for 16 hours to give the title compound. MS (LC-MS) m/e 308.0 (M+H)+.

According to the analysis of related databases, 89459-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie Inc.; Benatuil, Lorenzo; Bruncko, Milan; Chao, Debra; Izeradjene, Kamel; Judd, Andrew S.; Phillips, Andrew C.; Souers, Andrew J.; Thakur, Archana; (556 pag.)US2017/355769; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 61272-76-2, These common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, 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.

JV-Benzyl-2-iodo-5-methoxybenzamide (1.61 g, 4.38 mmol), 4-fluoror-2-iodoaniline (867 mg, 3.66 mmol), copper (I) iodide (139 mg, 0.73 mmol), and potassium carbonate (1.26 g, 9.12 mmol) were taken up in anhydrous DMSO (24 mL) and the resulting reaction mixture and the resulting reaction mixture was first stirred at 80 C for 2 hours, followed by heating to 135 C for another 16 hours. After cooling to room temperature, the mixture was filtered over celite and concentrated. The residue was diluted w th an excess of Et20 and washed with water. The organic layer was dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : Hex = 0: 100 to 100:0: then EtOAc : DCM = 0: 100 to 25:75) to give l0-Benzyl-8-fluoro-2-methoxy-5,10-dihydro-l li/- dibenzo[£>,e][l,4]diazepin-l l-one (565 rng, 44%) as a light yellow’ foam.

The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164953; (2019); A1;,
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 39998-81-7 as follows. name: 2-Fluoro-4-iodo-1-methylbenzene

Methyl-2-fluoro-4-iodo benzoate (Reagent G) A solution of 2-fluoro-4-iodo toluene (5 g, 26.6 mmol) in pyridine (2 mL) and water (20 mL) was treated with potassium permanganate (16.6 g, 105 mmol) and heated at 150 C. overnight. The reaction mixture was then cooled to room temperature and filtered and the filtrate was extracted with hexane. The aqueous phase was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in 20 mL of methanol, treated with concentrated sulfuric acid (1 mL) and refluxed overnight. The volatiles were distilled off in vacuo and the residue was dissolved in diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.26 g, 5%). 1H-NMR (300 MHz, CDCl3): delta7.60 (m, 4H), 3.93 (s, 3H).

According to the analysis of related databases, 39998-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1,1,1-Trifluoro-3-iodopropane

Example 25 (rac)-cis-9-(Phenylethynyl)-4-(3,3,3-trifluoropropyl)-3,4,4a,5,6,10b-hexahydro-2H-[1,4]oxazino[2,3-f]quinoline A mixture of cis-9-(phenylethynyl)-3,4,4a,5,6,10b-hexahydro-2H-[1,4]oxazino[2,3-f]quinoline (200 mg, 0.69 mmol), 1,1,1-trifluoro-3-iodopropane (202 mg, 0.90 mmol), and NaHCO3 (126 mg, 1.50 mmol) in DMF (3 mL) is stirred at 50-60 C for 6 hours. Then an additional amount of 1,1,1-trifluoro-3-iodopropane (100 mg, 0.45 mmol) is added, and the mixture is stirred at the same temperature for 16 h, cooled down to rt, diluted with water (50 mL) and extracted with EtOAc (2*50 mL). The combined organic layers are dried over Na2SO4 and concentrated at reduced pressure. The obtained residue is purified by column chromatography (silica gel, EtOAc/hexane, 1:2) to provide the title compound (75 mg, 28%) as a yellowish oil. 1H NMR (DMSO-d6), deltaH, 1.75-1.84 (m, 1H), 2.12-2.23 (m, 1H), 2.40-2.54 (m, 3H), 2.61-2.89 (m, 4H), 2.91-3.01 (m, 2H), 3.58-3.71 (m, 2H), 4.64 (d, 1H), 7.43-7.49 (m, 3H), 7.56-7.62 (m, 2H), 7.84 (d, 1H), 8.58 (d, 1H). LC/MS (M+H)+ = 387

The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merz Pharma GmbH & Co. KGaA; The designation of the inventor has not yet been filed; EP2650284; (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. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,3-Difluoro-5-iodobenzene

A solution of feri-butyl piperazine- l-carboxylate (2 g, 17.54 mmol), l,3-difluoro- 5-iodobenzene (4.2 g, 17.50 mmol), NaOtBu (2.5 g), BINAP (108 mg, 0.17 mmol), and Pd2(dba)3 (160 mg, 0.17 mmol) in toluene (20 mL) was stirred for 16 h at 80 C, then quenched by the addition of 40 mL FLO. The resulting solution was extracted with 2×40 mL of EtOAc, and the combined organic layers were concentrated under vacuum and purified with silica gel chromatography using EtOAc / hexane (1/2) to afford 3.1 g (59%) of the title compound as an off-white solid. LC-MS: (ES, m/z) 299 NMR (400 MHz, DMSO -d6) d 6.69 – 6.57 (m, 2H), 6.49 (tt, J = 9.3, 2.2 Hz, 1H), 3.42 (t, J = 5.3 Hz, 4H), 3.26 – 3.13 (m, 4H), 1.42 (s, 9H).

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, molecular formula is C9H9IO2, 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. Recommanded Product: Methyl 4-iodo-3-methylbenzoate

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10 mol%), 3-methyl-4 iodine benzoate Methyl ester (0.2 mmol, 1.0 equiv.), N-(2,3-epoxypropyl)phthalamide (0.6 mmol, 3.0 equiv.) and dried Dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was added. Heat to 80 C for 24 hours. After cooling the reaction vessel to room temperature, it was quenched with water (10 mL) with methyl tert-butyl ether (3× 10 mL) was extracted, dried over Na2SO4, filtered and concentrated in vacuo. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 2:1 (v/v),Obtained 42 mg of methyl 7-methyl-2-((1,3-dioxoisoindolin-2-yl)methyl)-2,3-dihydrobenzofuran-5-carboxylate (white solid, Yield 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5471-81-8, its application will become more common.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com