Tag: M.W=200-300

Application of 7425-53-8,Some common heterocyclic compound, 7425-53-8, name is Ethyl 4-iodobutanoate, molecular formula is C6H11IO2, 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: In a 5 mL round-bottom flask under argon containing zinc powder (197 mg, 3 mmol) and PdCl2(Amphos)2 (7 mg, 0.01 mmol) was added 2% PTS solution in water (1.5 mL). N,N,N’,N’-Tetramethylethylenediamine (TMEDA, 232 mg, 2 mmol) was added at rt followed by the addition of the alkyl halide (2 mmol) and the heteroaromatic halide (0.5 mmol). The flask was stirred vigorously at rt for the indicated time. The product was extracted with EtOAc.11 Silica gel (1 g) was added to the combined organic phase and solvents were removed under vacuum. The resulting dry, crude silica was introduced on top of a silica gel chromatography column to purify the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-iodobutanoate, its application will become more common.

Reference:
Article; Krasovskiy, Arkady; Thome, Isabelle; Graff, Julien; Krasovskaya, Valeria; Konopelski, Paul; Duplais, Christophe; Lipshutz, Bruce H.; Tetrahedron Letters; vol. 52; 17; (2011); p. 2203 – 2205;,
Iodide – Wikipedia,
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Application of 32024-15-0, 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. 32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The condensation reactions of halogenated dimethoxy benzaldehydeadducts (2a, 2b, or 2c) and 3-morpholinopropio nitrile (3) wereconducted based on the previously reported procedure.15 Compound 3(11.49 mmol), prepared based on previously reported procedure.20 wasdissolved in DMSO (3.0 mL) and heated to 65 C. Into a preheated solution,a freshly prepared sodium methoxide (4.59 mmol) was slowlyadded and stirred for 45 min at 80 C. Then, a solution of 2 (9.19 mmol)in DMSO (5.0 mL) was added into the heated solution. The reaction wasstirred at 80 C for 16 h. The reaction was quenched with diluted HCl(1:2 of 1M HCl in H2O) and extracted with CH2Cl2. An organic layerwas subsequently washed with water and saturated NaCl solution. Thewashed organic layer was dried over Na2SO4. The solvent was removedunder reduced pressure, affording dark brown viscous liquid. The crudeproduct was partially purified by column chromatography to give ayellow to brown viscous liquid mixture. The mixture was carried on tothe next step.

The chemical industry reduces the impact on the environment during synthesis 3-Iodo-4,5-dimethoxybenzaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nilchan, Napon; Phetsang, Wanida; Nowwarat, Taechin; Chaturongakul, Soraya; Jiarpinitnun, Chutima; Bioorganic and Medicinal Chemistry; vol. 26; 19; (2018); p. 5343 – 5348;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1018450-37-7, name is 4-Chloro-3-fluoro-2-iodoaniline, 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 1018450-37-7, Formula: C6H4ClFIN

To a solution of 4-chloro-3-fluoro-2- iodoaniline (300 mg, 1.105 mmol) in EtOAc (6.9 mL) was added to a solution of HCl (37% wt, 2.3 mL, 27.8 mmol) in water (6.9 mL) at 0C. The resulting mixture was stirred for 10 minutes. To this suspension was added a solution of sodium nitrite (84 mg, 1.216 mmol) in water (0.5 mL) over three minutes. The reaction was stirred for 30 min. A solution of sodium azide (79 mg, 1.216 mmol) in 0.5 mL water was added slowly to the above reaction mixture. The mixture was then stirred in an ice-water bath under nitrogen and allowed to warm to rt overnight. The mixture was extracted with ethyl acetate (2 x 30 mL). The combined organic fractions were washed with brine (30 mL) and dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to give the title compound.

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-Chloro-3-fluoro-2-iodoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13421-13-1, name is 4-Chloro-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 13421-13-1, Recommanded Product: 13421-13-1

4-chloro-2-iodobenzoic acid 7a (15 g, 53 mmol) was dissolved in dry THF (250 mL) and the solution was cooled to 0 C. Hereupon, NEt3 (1 1 mL, 80 mmol) and ethyl chloroformate (7.6 mL, 80 mmol) were added. The reaction was stirred for 1.5 hour and subsequently NaBH (8.0 g, 210 mmol) was added in four portions. After 1.5 hour, additional NaBH (4.0 g, 105 mmol) was added and the reaction was stirred for another hour. Hereupon, the reaction was quenched with H20 (100 mL) and EtOAc (200 mL) was added. The organic layer was washed with H20 (3 chi 150 mL), brine (100 mL) and subsequently dried over MgS04. The solvents were removed under reduced pressure and the crude product was obtained by gradient column chromatography (EtOAc/-heptane, 1 :9 to 1 :6). Compound 8a was obtained as white solid (8.4 g, 75% over 2 steps). 1H-NMR (400 MHz, CDC13) delta: 7.82 (s, 1H), 7.45-7.33 (m, 2H), 4.65 (d, J = 6.2 Hz, 2H), 1.94 (t, J = 6.2 Hz, 1H). 13C- NMR (75 MHz, CDC13) delta: 141.1, 138.3, 133.8, 128.8, 128.6, 96.9, 68.6. HRMS (EI+) m/z calcd for C7H60C1I [M]’+ 267.9152, found 267.9160.

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

Reference:
Patent; STICHTING KATHOLIEKE UNIVERSITEIT; SYNAFFIX B.V.; DEBETS, Marjoke Froukje; RUTJES, Floris Petrus Johannes Theodorus; VAN HEST, Jan Cornelis Maria; VAN DELFT, Floris Louis; VAN BERKEL, Sander Sebastiaan; WO2014/189370; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 626-62-0, These common heterocyclic compound, 626-62-0, name is Iodocyclohexane, 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: THF (1.5 mL), organic halide 3 (1.5 mmol, 1.0 equiv) and Ir(dtbbpy)(ppy)2 PF6 (3.5 mg, 0.0025 equiv) were successively added to a test tube containing Zn dust (73 mg, 1.125 mmol, 0.75 equiv). The reaction mixture was stirred under irradiation with a strip of 400 nm LEDs for 5 h, with water cooling to maintain the reaction temperature around 23-25 C. For the work-up, H2O (5 mL) was added and the mixture was extracted with hexane (3 ¡Á 7 mL). The combined extracts were filtered through Na2SO4 and concentrated under vacuum.The residue was purified by flash chromatography eluting with hexane/EtOAc.

The synthetic route of 626-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Levin, Vitalij V.; Agababyan, Daniil P.; Struchkova, Marina I.; Dilman, Alexander D.; Synthesis; vol. 50; 15; (2018); p. 2930 – 2935;,
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. 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9IO2

To a solution of aryl methoxy substituted aryl iodide (40 mmol) in isopropylamine (250 ml) were added Pd(PPh3)2Cl2 (0.4 mmol) and CuI (0.8 mmol), then trimethylsilylacetylene (44 mmol). The reaction mixture was stirred at ambient temperature for 2 to 4 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate, and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum/ethyl acetate as an eluent to give the methoxy substituted arylethylyl trimethylsilanes.

According to the analysis of related databases, 25245-27-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-55-7,Some common heterocyclic compound, 103440-55-7, name is Methyl 2-iodo-6-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.

Methyl 2-iodo-6-methylbenzoate (158) (2.00 g, 7.245 mmol) and NBS (1.418 g, 7.969 mmol) were stirred in chlorobenzene (50 mL) and benzoyl peroxide (75% w/w, 0.234 g, 0.724 mmol) was added. The reaction was stirred at 90 C for 18 hours, cooled to room temperature, filtered and the precipitate was washed with cyclohexane (4×10 mL). The combined filtrates were evaporated, and the resulting brown oil was diluted with THF (50 mL). Aqueous ammonia solution (20 mL) was added, and the mixture was stirred vigorously for 1 hours. The mixture was diluted with water (20 mL) and the THF was removed in vacuo. DCM (150 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (2x 00 mL), the combined organics were washed with brine (100 mL), dried (MgS04) and filtered. Silica gel was added and the volatiles were removed in vacuo to give the crude material absorbed onto silica gel. The material was purified by silica gel chromatography (Biotage Isolera, 40 g Si cartridge, 0-100% EtOAc in petroleum benzine 40-60 “C, then 0-20% methanol in EtOAc) to give the title compound (159) (0.757 g, 40% yield) as a beige solid; 1H NMR (400 MHz, CDCI3) delta 7.93 (dd, J = 7.8, 0.7 Hz, 1 H), 7.46 (dd, J = 7.5, 0.8 Hz, 1 H), 7.26 – 7.21 (m, 1 H), 7.10 (br s, 1 H), 4.37 (d, J = 0.6 Hz, 2H). LCMS Method C: rt 5.06 min; m/z 260.0 IM+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-iodo-6-methylbenzoate, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 144550-76-5, 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. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

C. 4-Iodo-2-(Quinoxaline-5-sulfonylamino)benzoic acid methyl ester. A solution of methyl 2-amino-4-iodobenzoate (1.2 g, 4.4 mmol), quinoxaline-5-sulfonyl chloride (1.2 g, 5.3 mmol), pyridine (1.7 mL, 22 mmol) and DCM (25 mL) was maintained at 23 C. for 24 h. The reaction mixture was diluted with DCM (200 mL) and washed with satd. aq. NaHCO3, then dried and concentrated to a tan solid. This residue was chromatographed (0 to 100% EtOAc/CH2Cl2) to afford the sulfonamide as a light yellow solid (1.6 g, 77%). MS (ESI): calculated for C16H12IN3O4S, 469.0; m/z found, 470 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.10 (s, 1H), 9.07 (d, J=1.8 Hz, 1H), 9.01 (d, J=1.8 Hz, 1H), 8.60 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (dd, J=8.5, 1.3 Hz, 1H), 8.04 (dd, J=7.5, 1.0 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.37 (dd, J=8.3, 1.6 Hz, 1H), 3.88 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); 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. 116632-39-4, name is 5-Bromo-2-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-2-iodotoluene

In dioxane (5 mL) solution of tert-butyl 5-hydroxy-4-methyl-2,3-dihydro-1H-indole-1-carboxylate (250 mg) and 5-bromo-2-iodo toluene (212 muL), copper iodide (I) (38.1 mg), N,N-dimethyl glycine (41.2 mg), cesium carbonate (651 mg) was added and stirred for 24 hours at 100 C. The reaction mixture into a saturated ammonium chloride solution (6 mL), saturated aqueous sodium bicarbonate (3 mL), and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After washing the resulting residue with hexane, collected by filtration, and dried to give the title compound (57.5 mg) as a white solid.

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 116632-39-4.

Reference:
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; GOTO, TAIJI; SASAKI, JUNKO; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (97 pag.)JP2016/108257; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-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.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 oC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 105-107 C; 1H NMR (400 MHz, CDCl3) delta 8.09 (s, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 3.73 (s, 2H), 3.30(s, 2H), 2.40 (s, 3H), 1.07 (s, 6H); 13C NMR (100 MHz, CDCl3) delta 161.6, 136.5, 134.6, 131.2, 129.7, 124.1, 122.0, 57.0, 52.5, 27.9, 24.2, 20.8 ppm. Anal. Calcd. for C14H16N2OS: C 64.58, H 6.19, N 10.76; found: C 64.25, H 6.27, N 10.49; EI-MS: m/z = 260 (M+)

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com