Tag: M.W=200-300

Electric Literature of 204257-72-7, These common heterocyclic compound, 204257-72-7, name is Methyl 2-fluoro-4-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.

To a single neck flask were added 4-bromo-2-fluorobenzene boronic acid (0.50 g, 2.28 mmol), methyl 2-fluoro-4-iodobenzene carboxylate (0.57 g, 2.06 mmol), potassium carbonate (0.95 g, 6.87 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (84 mg, 0. 11 mmol). The reaction mixture was stirred at 100 C for 1 hour and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 100/1) to give the title compound as colorless (0.39 g, 52%).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; LIU, Xinchang; HUANG, Jianzhou; ZHANG, Yingjun; GOLDMANN, Siegfried; (342 pag.)WO2019/1396; (2019); 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. 608-28-6, name is 2-Iodo-1,3-dimethylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Iodo-1,3-dimethylbenzene

General procedure: Catalyst 1a22a (43 mg, 0.1 mol % of supported palladium) was added to a solution of aryl iodide (0.40 mmol, 1.0 equiv), aryltrialkoxysilane (0.80 mmol, 2.0 equiv), TBAF·3H2O (252 mg, 0.8 mmol, 2.0 equiv) in a mixture of toluene (5 mL) and H2O (50 muL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, 1a was filtered under vacuum on a 0.2 mum membrane. The catalyst was successively washed with toluene (10 mL) and Et2O (10 mL). The combined organic phases were washed with H2O (20 mL), dried with MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash-chromatography on silica gel. Catalyst 1a was dried under vacuum and can directly be used for another Hiyama coupling.

The synthetic route of 608-28-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diebold, Carine; Derible, Antoine; Becht, Jean-Michel; Le Drian, Claude; Tetrahedron; vol. 69; 1; (2013); p. 264 – 267;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 35674-27-2, A common heterocyclic compound, 35674-27-2, name is 4-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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.

Example 14 Preparation of N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1) 10 g (0.034 mol) 4-Iodo-3-nitrobenzoic acid (Compound VI-1) and 50 ml N,N-dimethylformamide were added into a reaction flask, stirred to dissolve, and cooled to below 10 C., and 7.5 ml (0.10 mol) sulfoxide chloride was added. After completion of the dropwise addition, the mixture was warmed to room temperature and reacted for one hour. The reaction mixture was poured into 200 ml aqueous solution of 30% methylamine with low temperature, stirred for 5 minutes to precipitate a solid, and then the mixture was added with 500 ml ice-water, stirred for 10 minutes, filtered. The solid was washed with water and dried to obtain N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1), 6.5 g (0.021 mol), yield 62.3%. 1HNMR (400 MHz, DMSO-d6): delta 2.81 (d, 3H, J=4.1 Hz), 7.84 (d, 1H, 7.8 Hz), 8.23 (d, 1H, J=8.1 Hz), 8.33 (s, 1H), 8.75 (s, 1H); MS (m/z): 307 [M+H].

The synthetic route of 35674-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd.; Bai, Hua; Zhao, Xuyang; Gong, Yongxiang; Zhong, Jinqing; Zhu, Qifeng; Liu, Xiaoyu; Liu, Lifei; Zhou, Qixian; US2013/225810; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

[0115] To a stirred solution of (Z)-4-(l-(4-(methoxymethoxy)phenyl)-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde (12 g, 28.4 mmol, with – 10- 15% of another regioisomer) in 2-methyltetrahydrofuran (120 mL) were added 2-chloro-4- fluoro-l-iodobenzene (5.5 mL, 40.5 mmol) and KOH (45 mL, 3M aqueous solution, 142.2 mmol). The resultant mixture was degassed with argon for 10 min followed by the addition of PdCl2(PPh3)2 (0.7 g, 2.84 mmol). After stirring at 60C for 12 h, the mixture was cooled to rt and quenched with water:EtOAc (1 : 1, 100 mL). The organic layer was separated, washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The crude compound was purified by chromatography (Si02, 10% EtOAc/hexane) to afford (E)-4-(2-(2- chloro-4-fluorophenyl)- 1 -(4-(methoxymethoxy) phenyl) but- 1 -en- 1 -yl)benzaldehyde as a pale yellow solid (6.0 g, 67% with -10-15% of the other regioisomer). Major isomer: XH NMR (400 MHz, CDC1 ) delta 9.84 (s, 1H), 7.55 (d, = 8.0 Hz, 2H), 7.20 – 7.17 (m, 2H), 7.10 (d, = 8.0 Hz, 2H), 7.04 – 6.97 (m, 4H), 6.84 – 6.80 (m, 1H), 5.19 (s, 2H), 3.50 (s, 3H), 2.55 – 2.45 (m, 2H), 0.97 – 0.93 (m, 3H); MS (ESI) m/z 425.19 [M+H]+.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HEGDE, Sayee, Gajanan; HOPKINS, Chad, Daniel; (76 pag.)WO2019/23481; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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 33348-34-4, Application In Synthesis of 4-Amino-3-iodobenzonitrile

To a 500 mL three-necked round bottom flask containing DMF (195 mL) (deoxygenated with N2 and slight vacuum) were sequentially added 4-amino-3-iodobenzonitrile (12.2 g, 50.0 mmol), pyridine 4-methylbenzenesulfonate (0.477 g, 1.9 mmol), tetraethoxysilane (13.23 g, 63.5 mmol), and ethyl 2-(2-oxocyclopentyl)acetate (12.76 g, 75.0 mmol) under N2. The reaction mixture was heated at 135 C in the dark overnight. To the mixture were added N- ethyl-N-isopropylpropan-2 -amine (26.2 mL, 150 mmol) and palladium (II) acetate (0.337 g, 1.5 mmol) under N2. The resulting mixture was cooled to 120 0C and stirred for additional 16 h. The reaction mixture was cooled to room temperature and acidified to pH ~ 5 with 1 N aq. HCl. The solvent was evaporated under reduced pressure at 60 0C. To the resulting liquid residue was added water (300 mL) and EtOAc (500 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 400 mL). The combined organic layers were dried over Na2SO4, decanted and concentrated under reduced pressure to afford a dark brown liquid (22.1 g). The crude liquid was passed through a silica gel plug and eluted with 10%-40% EtOAc in hexanes. Fractions were concentrated and further purified by precipitation in DCM/hexanes to yield the title compound as a light orange solid (4.65 g). LCMS m/z = 269.2 [M + H]+; 1H NMR (400 MHz, DMSO-J6) delta ppm 1.19 (t, J = 7.12 Hz, 3H), 2.05-2.18 (m, IH), 2.54 (dd, J = 16.44, 8.45 Hz, IH), 2.64-2.85 (m, 4H), 3.52-3.63 (m, IH), 4.12 (q, J = 7.12 Hz, 2H), 7.34 (dd, J = 8.45, 1.58 Hz, IH), 7.49 (d, J = 8.45, IH), 7.85 (d, J = 0.81, IH), 11.30 (s, IH).

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, 4-Amino-3-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/78983; (2009); 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 31599-61-8 as follows. SDS of cas: 31599-61-8

General procedure: In a typical experiment the catalyst (containing 2.8 lmol Pd) was placed in a stainless steel autoclave. The aryl iodide (0.2 mmol), amine (0.5 mmol), base (35 ll, 0.25 mmol) and solvent (1 ml) were transferred into it under an inert atmosphere. It was charged with carbon monoxide (30 bar or 5 bar) and heated with stirring in an oil bath at 100 C or 120 C. After cooling to room temperature the catalyst was removed by filtration and was reused without further purification if the product was soluble in the solvent. In other cases, the solid material was washed by acetone and the catalyst was dried in vacuo prior to reuse. The reaction mixture was analyzed by gas chromatography.

According to the analysis of related databases, 31599-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Urban, Bela; Skoda-Foeldes, Rita; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 4-6; (2019); p. 302 – 306;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products 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.

5-Iodo-2-chlorobenzoic acid (20.0 g, 0.071 mol) was added to a solution of 2.0 M oxalyl chloride in dichloromethane (39 ml, 0.078 mol), stirred for suspension, and then 8 drops of DMF solution was added dropwise. After the reaction was carried out for 3 hours, the solution was clarified and the reaction was almost complete. The solvent was spin-dried on a rotary evaporator, then 15 ml of methylene chloride was added, and the solvent was dried. After spin-drying, add 30 ml of dichloromethane, stir, cool to 0-5 ° C, add fluorobenzene (7. lg, 0.074 mol), add anhydrous aluminum trichloride (9.9 g, 0.074 mol) in batches, control The temperature is not more than 5 °C, after the completion of the addition, stirring is continued at 4 ° C for 1 h, the reaction is almost complete by TLC, the reaction is quenched on ice-water mixture, the organic phase is separated, and the aqueous phase is extracted with dichloromethane. The phase was washed twice with 1 mol/L hydrochloric acid, washed once with water, and washed twice with 1 mol/L NaOH solution.The mixture was washed twice with saturated sodium chloride and dried over anhydrous sodium sulfate. Drain filtration, spin dry solvent to obtain oilAfter column chromatography, 20. 1g (78.6percent) of a white solid was obtained.

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

Reference:
Patent; Huarun Shuang He Pharmaceutical Co., Ltd.; Zhai Jianguo; He Yang; Zhu Yingjie; Zhou Yisui; Ma Hongmin; Song Meng; (46 pag.)CN108218928; (2018); 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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 52548-63-7

To a solution of 5-fluoro-2-iodobenzoic acid (17 g) obtained in Step A of Reference Example 1, copper(I) iodide (2.434 g), potassium carbonate (26.5 g) and N,N,N?,N?tetramethylethylene diamine (3.83 mE) in N,N-dimethylformamide (200 mE) was added 1H-1,2,3-triazole (11.11 mE), and the mixture was stirred overnight at 1000 C. The reaction mixture was filtered through Celite, to the filtrate was added 6N aqueous hydrochloric acid solution at 0 C., and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ ethyl acetate) to give the title compound (5.6 g). 1H NMR (300 MHz, DMSO-d6) delta 7.52-7.69 (2H, m), 7.81 (1H, dd, J=8.7, 4.9 Hz), 8.08 (2H, s), 13.35 (1H,brs).

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 52548-63-7.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 6940-76-7, The chemical industry reduces the impact on the environment during synthesis 6940-76-7, name is 1-Chloro-3-iodopropane, I believe this compound will play a more active role in future production and life.

4-(3-Chloropropyl)-7-fluoro-4H-benzo[1.4]oxazin-3-one A reaction flask was charged with 6,7-difluoro-4H-benzo[1.4]oxazin-3-one (1.5 g, 8.1 mmol), 1-chloro-3-iodopropane (1.44 g, 8.1 mmol), and Cs2CO3 (4.0 g, 12.2 mmol) in MeCN (10 mL) and stirred at rt for 40 h. The reaction mixture was concentrated, water added, and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (1.88 g, 89%). 1H NMR (CDCl3) d 6.99 (dd, J=8.0 Hz, J=5.6 Hz, 1H), 6.79-6.72 (m, 2H), 4.59 (s, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H) 2.18-2.10 (m, 2H); 13C NMR (CDCl3) d 163.9, 159.1 (d, J=244.1 Hz), 146.4 (d, J=11.9 Hz), 124.9 (d, J=3.0 Hz), 115.4 (d, J=9.6 Hz), 109.5 (d, J=22.7 Hz), 105.4 (d, J=26.2 Hz), 67.7, 42.4, 39.2, 30.1.

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, 1-Chloro-3-iodopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Skjaerbaek, Niels; Koch, Kristian Norup; Mikael Friberg, Bo Lennart; Tolf, Bo-Ragnar; US2005/209226; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 216393-67-8,Some common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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 65 – PREPARATION of A/-(2-(5-Chloro-7-fluoro-2-(triethylsilyl)-1H-indol-3- yl)ethyl)-4-(3-fluorobenzyl)benzamide. 4-Chloro-2-fluoro-6-iodoaniline (0.100 g; 0.368 mmol), 4-(3-fluorobenzyl)-N-(4- (triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.368 mmol), bis(diphenylphosphino)ferrocene]palladium(ll) chloride (0.015 g; 0.018 mmol), lithium chloride (0.016 mg; 0.368 mmol) and sodium carbonate (0.078 g; 0.737 mmol) were suspended in DMF (5 ml_) and the mixture was stirred at 100C for 18 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60 % ethyl acetate in heptane) to afford 0.102 g (51 %) of the title compound as a yellow oil. ESI/APCI(+): 539(M+H).

The synthetic route of 216393-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D; REMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; ALLASIA, Sara; MARCHAND, Arnaud; KILONDA, Amuri; CHALTIN, Patrick; WO2012/80221; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com