Tag: M.W=200-300

Electric Literature of 1798-06-7, These common heterocyclic compound, 1798-06-7, name is 2-(4-Iodophenyl)acetic acid, 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 stirred solution of 2-(4-iodophenyl)acetic acid (2.00 g, 7.63 mmol) in tetrahydrofuran (150 ml_) at room temperature was added borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 7.63 ml_, 7.63 mmol). The resulting solution was stirred for 6 hours prior to dilution with brine, adjustment to pH = 13 with NaOH, and extraction with ethyl epsilonicetate. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford 192a (620 mg, 33%) as a light orange solid which was used in the subsequent reaction without further purification. LRMS (ESI): (calc) 248.1 ; (found) 271.1 (M+Na)+

Statistics shows that 2-(4-Iodophenyl)acetic acid is playing an increasingly important role. we look forward to future research findings about 1798-06-7.

Reference:
Patent; METHYLGENE INC.; WO2006/102760; (2006); A1;,
Iodide – Wikipedia,
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Related Products of 239135-53-6,Some common heterocyclic compound, 239135-53-6, name is 2-Fluoro-4-iodo-1-(trifluoromethyl)benzene, molecular formula is C7H3F4I, 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 79: 3,4-bis(Benzyloxy)-6-[(E)-2-[3-fluoro-4-(trifluoromethyl)-phenyl]ethenyl]pyridazine[0511][0512]A vessel containing 3,4-bis(benzyloxy)-6-ethenylpyridazine (Intermediate 78, 1.09 g, 3.42 mmol), tris-(2-methylphenyl)phosphane (0.208 g, 0.685 mmol), 2-fluoro-4-iodo-1-(trifluoromethyl)benzene (1.191 g, 4.11 mmol) and palladium(II) acetate (0.038 g, 0.171 mmol) was evacuated and acetonitrile (10 ml) and triethylamine (9.07 ml, 65.1 mmol) were added in vacuo and then the mixture was flushed with nitrogen. The reaction was then heated in the microwave at 80 C. for 4 hours and, upon cooling, was diluted with dichloromethane and washed with saturated aqueous ammonium chloride solution. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil which was purified by column chromatography (silica, eluting with 30-100% dichloromethane in petrol) to yield 3,4-bis(benzyloxy)-6-[(E)-2-[3-fluoro-4-(trifluoromethyl)phenyl]ethenyl]pyridazine (1.1 g, 2.29 mmol, 67% yield).[0513]1H NMR (CDCl3) delta 7.53-7.68 (m, 3H), 7.31-7.53 (m, 12H), 6.97 (s, 1H), 5.71 (s, 2H) and 5.28 (s, 2H).[0514]MS ES+: 481.

The synthetic route of 239135-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FARNABY, William; FIELDHOUSE, Charlotte; KERR, Catrina; KINSELLA, Natasha; LIVERMORE, David; MERCHANT, Kevin; MILLER, David; HAZEL, Katherine; US2013/52281; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

42048-11-3, name is 2-Chloro-6-iodotoluene, 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. Application In Synthesis of 2-Chloro-6-iodotoluene

N-Bromosuccinimide (NBS, 3.52 g, 19.8 mmol) and benzoyl peroxide (39 mg, 0.16 mmol) were added to a solution of 1-chloro-3-iodo-2-methylbenzene10e (5 g, 19.8 mmol) in CCl4 (55 mL). The mixture was heated to reflux for 15 hours then cooled to room temperature. The suspension was filtered and the filtrate concentrated under reduced pressure to yield a yellow waxy solid. (6.0 g, 92%yield). This material was used without further purification in subsequent reactions. 1H NMR (400MHz, CDCl3): d 7.78 (d, 1H), 7.39 (d, 1H), 6.92 (t, 1H), 4.82 (s,2H); LRMS m/z 330/332 [M+H]+; Also a known commercially available compound.

The synthetic route of 42048-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roberts, Lee R.; Corbett, Matthew S.; Fussell, Steven J.; Hitzel, Laure; Jessiman, Alan S.; Mason, Helen J.; Osborne, Rachel; Ralph, Michael J.; Stennett, Adam S.D.; Wheeler, Simon; Storer, R. Ian; Tetrahedron Letters; vol. 56; 47; (2015); p. 6546 – 6550;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 1031929-20-0, name is 4-Fluoro-2-iodobenzonitrile, molecular formula is C7H3FIN, 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: 1031929-20-0

Reference Intermediate Rll4-hvdroxy-2-iodobenzonitrileTo a solution of 2-fluoro-4-iodobenzonitrile (5.0 g, 20.24 mmol) in dry acetonitrile (100 mL) potassium trimethylsilanolate (1.18 g) was added and the reaction mixture was stirred overnight at 50C. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and an aqueous pH 3 buffer solution was added up to pH ~5. Two phases were separated and the organic layer was dried (Na2S04), filtered and evaporated to afford the title compound (4.90 g) as brown solid.XH NMR (400 MHz, DMSO-c/6): delta ppm 10.92 (1H, s), 7.65 (1H, d), 7.39 (1H, d), 6.93 (1H, dd); UPLCjpqc: 0.81 min, 244 [M-H]-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1031929-20-0, its application will become more common.

Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; ALVARO, Giuseppe; DAMBRUOSO, Paolo; MARASCO, Agostino; TOMMASI, Simona; DECOR, Anne; LARGE, Charles; WO2012/76877; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 459424-72-7,Some common heterocyclic compound, 459424-72-7, name is 1,2,3-Trifluoro-4-iodobenzene, molecular formula is C6H2F3I, 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 25 mL reaction tube, Mn(OAc)3.2H2O(10 mol%), DABCO (2.5 equiv.) and a stirring bar were added. Then iodobenzene(1 mmol), phenyl acetylene (1 mmol) and PEG-400 were injected by syringe. The reaction tube was closed and transferred to a 70 C oil bath for 19-24 hours. After the reaction completed, cool down the reaction mixture to room temperature. Water (2 mL) was added and the reaction mixture was extracted with ethyl acetate and then concentrated and purified by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,3-Trifluoro-4-iodobenzene, its application will become more common.

Reference:
Article; Qi, Xinxin; Jiang, Li-Bing; Wu, Xiao-Feng; Tetrahedron Letters; vol. 57; 15; (2016); p. 1706 – 1710;,
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. 5469-33-0, name is (Iodomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Safety of (Iodomethyl)cyclohexane

In the same manner as in Preparation Example 70-2, the objective compound (797 mg, 56%) was obtained as a colorless oil from 4-bromo-1-((tert-butyldiphenylsilyloxy)methyl)-2-chlorobenzene and cyclohexylmethyl iodide. 1H-NMR(CDCl3): 0.82-1.75(11H, m), 1.11(9H, s), 2.45(2H, d, J=7 Hz), 4.79(2H, s), 7.03-7.11(2H, m), 7.31-7.48(6H, m), 7.61(1H, d, J=8 Hz), 7.63-7.73(4H, m)

According to the analysis of related databases, 5469-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6348474; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 835595-11-4, A common heterocyclic compound, 835595-11-4, name is 3,4-Dichloro-2-iodoaniline, molecular formula is C6H4Cl2IN, 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.

[0106] (a) To a solution of 3,4-dichloro-2-iodoaniline (example 2, 2.2 g, 7.67 mmol) in dry pyridine (8 mL) was added 4-tert-butyl-3-fluorophenylsulfonyl chloride (2.11 g, 8.43 mmol) and the reaction mixture was heated at 80 0 C for overnight. LCMS indicated presence of mono and bis-sulfonamides. 10 N aq. NaOH (3 mL) and ethanol (2 mL) were added to hydrolyze the bis-sulfonamide. The reaction mixture was then heated at 80 C for 2 h. It was cooled to r.t, excess solvent was removed in vacuo to afford a dark brown solid, diluted with DCM, washed with IN aq.HCl, and purified by flash column using hexanes: ethyl acetate mixture as an eluent on silica column to get the pure 4-tert-butyl-N-(3,4-dichloro-2- iodophenyl)-3-fluorobenzsulfonamide as an off white solid (3.5 g, 91%)

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; CHEMOCENTRYX, INC.; DAIRAGHI, Daniel; DRAGOLI, Dean, R.; KALISIAK, Jarek; LANGE, Christopher, W.; LELETI, Manmohan, Reddy; LI, Yandong; LUI, Rebecca, M.; MALI, Venkat, Reddy; MALATHONG, Viengkham; POWERS, Jay, P.; TANAKA, Hiroko; TAN, Joanne; WALTERS, Matthew, J.; YANG, Ju; ZHANG, Penglie; WO2015/84842; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 172681-47-9, 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. 172681-47-9, name is 2-Amino-6-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows.

[00266] N-Acetyl-3-Iodo-2-Methyl Aniline. Charge a 5 L, 3 neck flask equipped with a mantle, stirrer, condenser, with 708 grams (5M) 3-Iodo-2-Methyl Aniline, followed by 700ml glacial acetic acid. Add in a stream of 520 grams (5.1M) acetic anhydride and allow the solution to come to a gentle reflux for an hour. The solution is allowed to cool and poured in a stream in a large container of 8L ice water. The product will crystallize immediately and is filtered and squeezed under vacuum and air-dried. Yield was 900 grams (Theoretical yield = 918 g).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-iodotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LATHAM, Keith, R.; WO2013/10102; (2013); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 914636-93-4, A common heterocyclic compound, 914636-93-4, name is 3-Fluoro-5-iodobenzaldehyde, molecular formula is C7H4FIO, 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.

3-Fluoro-5-iodobenzaldehyde, monomethyl malonate, and a catalytic amount of pyrrolidine are heated in pyridine. After cooling, the solvent is distilled off in vacuo. 2N HCl and ethyl acetate are added to the residue, and the phases are separated. The organic layer is washed with brine and dried over Na2SO4. After evaporation, the residue is purified by CC on silica gel with EtOAc/hexane. Evaporation of appropriate fractions yields the title compound.

The synthetic route of 914636-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PSYCHOGENICS, INCstatuts; CHANDRASEKHAR, Jayaraman; KOZIKOWSKI, Alan, P.; LIU, Jianhua; TUECKMANTEL, Werner; WALKER, Joel, R.; YUEN, Po-wai; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; WO2010/45212; (2010); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 773855-64-4, name is 1-Fluoro-4-iodo-2-methoxybenzene, 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 773855-64-4, name: 1-Fluoro-4-iodo-2-methoxybenzene

Dissolve 1-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (480 mg, 1. 9 mmol) in triethylamine (7 mL, 53 mmol) and add 3- chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (250 mg, 1. 8 mmol) followed by bis (triphenylphosphine) palladium (II) dichloride (51 mg, 0. 07 mmol) and copper (I) iodide (28 mg, 0. 15 mmol). Stir for 18 h at room temperature, concentrate, and purify by silica gel chromatography, eluting with 3 : 1 hexanes : ethyl acetate. Further purify on silica gel, eluting with 100% dichloromethane, to give the title compound as a white solid (450 mg, 94%). 1H NMR (300 MHz, CDC13) 6 3. 93 (s, 3H), 7. 04-7. 14 (m, 3H), 7. 79-7. 81 (m, 1H), 8. 51 (d, J = 2. 3 Hz, 1H), 8. 62 (d, J = 1. 7 Hz, 1H) ; MS (APCI) : m/z = 262 [M+H] +.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com