Tag: M.W=200-300

69113-59-3, name is 3-Iodobenzonitrile, 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. Computed Properties of C7H4IN

General procedure: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL × 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
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101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, 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. Recommanded Product: 101335-11-9

The 1-(2-chloro-4-fluorophenyl)-2-piperazinone used in the above procedure was prepared as follows: A suspension of 2-piperazinone (1.5 g, 15.0 mmol), 2-chloro-4-fluoro-1-iodobenzene (3.8 g, 15.0 mmol), copper(l) iodide (0.57 g, 3.0 mmol), N,N’-dimethyl-1 ,2- cyclohexanediamine (1.3 g, 6.0 mmol), and potassium phosphate (6.4 g, 44.9 mmol) in 1 ,4-dioxane (20 ml) was heated at reflux (1000C) under argon for 20 hours. The mixture was allowed to cool to room temperature and then diluted with dichloromethane and 0.88M ammonia diluted in water (1 :5). The mixture was extracted into dichloromethane (x3), and then the combined organic extracts were washed with water (x2) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the crude product was purified by flash-silica gel chromatography, eluting with 5% 2M ammonia in methanol in dichloromethane, to give the product 1-(2-chloro-4-fluorophenyl)-2-piperazinone (250mg) as a brown oil which was used without further purification. LC/MS [M+H]+ = 229.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53459; (2009); A1;,
Iodide – Wikipedia,
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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., Recommanded Product: Methyl 2-amino-5-iodobenzoate

methyl 4-amino-4′-propyl-[l,l’-biphenyl]-3-carboxylate (4a) Synthesized using reported procedure with modification (US Patent Application Publication Culshaw et al, Pub. No. US 2008/0293939 Al, Nov 27, 2008). To a round-bottom-flask under nitrogen methyl 2-amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), 4- propylphenylboronic acid (541 mg, 3.3 mmol, 1.1 equiv.) and DMF (20 mL) were added, followed by addition of catalyst Pd(dppf)Cl2 (110 mg, 0.15 mmol, 0.05 equiv.) and the mixture were stirred for 15 minutes. 2M Na2CC>3 solution (7.5 mL, 15 mmol, 5.0 equiv.) was added and then the mixture was heated at 80 C for 16 hours. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was filtered and concentrated under reduced pressure. H20 (20 mL) was added to the residue which was extracted with EtOAc (2 x 20 mL). All the organic extracts were combined, dried over NaSC>4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=20:80) on silica gel to afford 4a (418 mg, 51%) as yellow solid. XH NMR (400 MHz, CDCI3) delta 8.11 (s, 1H), 7.53-7.20 (m, 5H), 6.71 (d, J= 8.0 Hz, 1H), 5.74 (s, 2H), 3.88 (s, 3H), 2.60 (t, J= 8.0 Hz, 2H), 1.71-1.61 (m, 2H), 0.96 (t, J = 8.0 Hz, 3H); 1 C NMR (100 MHz, CDCI3) delta 168.56, 149.48, 140.96, 137.74, 132.70, 129.37, 129.23, 128.81, 126.03, 117.13, 110.90, 51.54, 37.61, 24.55, 13.82.

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 77317-55-6.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
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Electric Literature of 156150-67-3, 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 156150-67-3 as follows.

EXAMPLE 42-(2-Chloro-4-iodorhohenylaminoV5.5-dimethyl-8-oxo-5,6J.8-tetrahvdro-4H-thienor2,3- clazepine-S-carboxylic acid ethyl ester; Caesium carbonate (2.77 g, 8.51 mmol) and 2-chloro-4-iodo-l-fluorobenzene (2.18 g, 8.51 mmol) were added to a solution of Intermediate 6 (2.0 g, 7.09 mmol) in DMF (20 mL) and heated at 650C for 18 h. Brine (100 mL) was added to the reaction and the mixture extracted with DCM (3 x 50 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residual DMF was azeotroped with heptane. The crude product was purified by chromatography (silica, 0-30% EtOAc in DCM) to give the title compound as a cream solid (916 mg, 25%). deltaeta (DMSO-d6) 10.60 (IH, s), 8.01 (IH, t, J 5.0 Hz), 7.95 (IH, d, J2.0 Hz), 7.78 (IH, dd, J 8.6, 2.0 Hz), 7.54 (IH, d, J 8.6 Hz), 4.32 (2H, q, J 7.1 Hz), 2.91 (2H, s), 2.85 (2H, d, J 5.2 Hz), 1.33 (3H, t, J 7.1 Hz), 0.99 (6H, s). LCMS (ES+) RT 3.81 minutes, 519 (M+H)+.

According to the analysis of related databases, 156150-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2008/20206; (2008); A2;,
Iodide – Wikipedia,
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Related Products of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 2-(4-nitrophenyl)acetate (6 g, 31 mmol) in DMF (100 ml) was cooled to 0 C with an ice bath. NaH (60% in oil) (2.5 g, 63 mmol) was added portion wise. The resulting mixture was allowed to warm to RT and was stirred for 15 min at RT. After 15 min the mixture was cooled again to 0 C and 1,3-diiodopropane (6 ml, 52 mmol) was added drop wise. The resulting mixture was allowed to stir at 0 C for 30 min, and from 0 C to 10 C for 1.5 h. After 1.5 h the solution was cooled to 0 C and water was added. The reaction mixture was extracted 3 times with DCM. The combined organics were concentrated under reduced pressure and the residue was purified by flash chromatography on silica (120 g flash column, 0-20% EtOAc in hexane, 10 CV) to afford methyl 1-(4-nitrophenyl)cyclobutanecarboxylate.

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); A1;,
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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. 5326-47-6, name is 2-Amino-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5326-47-6

The starting material 2-amino-5-iodo benzoic acid (1) (15mmol, 4 . 0g) is added to 15 ml of anhydrous methanol solution, then added to this solution in 3M the mass fraction of the 70% concentrated sulfuric acid. Heating to reflux 6h, then room temperature stirring 12h. After the completion of reaction, reducing pressure and evaporating solvent, then added to the residues in the bottle 100 ml saturated sodium bicarbonate solution, ethyl acetate (3×30 ml) extraction. Obtaining organic layer, saturated salt water (3×20 ml) washing, layered takes organically phase is dried with anhydrous sodium sulfate. Filtering, by reduced pressure evaporation to dry solvent to obtain 2-amino-5-iodo benzoic acid methyl ester (2) crude 3.96g, yield: 94.5%

The synthetic route of 5326-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Liu, Xinyong; Zhan, Peng; Kang, Dongwei; (22 pag.)CN105669653; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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 103962-05-6, Recommanded Product: 1-Iodo-4-(trifluoromethoxy)benzene

A solution of 4-bromophenol (0.173 g) in 4 mL of 1-methyl-2-pyrrolidone under argon atmosphere was treated with 4-(trifluoromethoxy)iodobenzene (0.313 mL), 2,2,6,6-tetramethylheptane-3,5-dione (0.046 mL) and caesium carbonate (0.652 g). The slurry was degassed by bubbling argon for 15 min and copper(I) chloride (0.099 g) was added. The reaction mixture was degassed by bubbling argon for 15 min, then heated to 100° C under argon for 5 h. The reaction mixture was cooled to room temperature and added dropwise to 30 mL of tert-butyl-methyl-ether. The slurry was filtered and the solids washed with tert-butyl-methyl-ether (3×20 mL). The combined filtrates were washed subsequently with 1N NaOH (50 mL), water (50 mL), 2N HCl (50 mL), 1N HCl (50 mL), water (50 mL) and brine (50 mL). The resulting organic layer was dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel eluting with hexane to afford 0.15 g of the title compound as a colourless liquid. 1H-NMR(d, ppm, CDCl3): 7.45(m, 2H); 7.20(m, 2H); 6.99(m, 2H); 6.90(m, 2H)

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

Reference:
Patent; GLAXO GROUP LIMITED; EP1862459; (2007); 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. 21304-38-1, name is 4-Iodobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodobenzene-1,2-diamine

A mixture of hexaketocyclohexane octahydrate (2.21 g, 7.08 mmol) and 4-Iodo-benzene-1,2-diamine (4.97 g, 21.24 mmol) was added to a degassed acetic acid (140 mL). The mixture was heated to 110 C for 3 hrs under nitrogen. After cooled to room temperature, the solid was collected by filtration and was washed with acetic acid to give a green solid (5.35 g, 99 % yield). ¹H (300 MHz, CD3Cl/CF3COOD) No. 9.11 (br, 3H), 8.54 (br, 3H), 8.32 (br, 3 H). HRMS EI: m/z calcd for C24H913N6 761.8023, Found 761.8087.

According to the analysis of related databases, 21304-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; WO2005/123737; (2005); A2;,
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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 90347-66-3

Unit Operation 1.1: 1 Sonogashira Reaction AP24595, palladium tetrakis triphenylphosphine (Pd(PPh3)4) , copper (I) iodide (Cul), triethylamine, and tetrahydrofuran (THF) are charged to the reactor. The mixture is stirred and degassed with nitrogen and then pre-degassed AP28141 is charged. The resulting mixture is brought to 45 – 55C and held for not less than 3 hours. The reaction completion is determined by IPC-1 (HPLC). If the IPC-1 criterion is met, the mixture is concentrated to a target volume and cooled. Unit Operation 1.2: Deprotection / 2nd Sonogashira Reaction AP25570, additional palladium tetrakis triphenylphosphine (Pd(PPh3)4), copper (I) iodide (Cul), and tetrahydrofuran (THF) are charged to the reactor. The mixture is concentrated and the water content is determined by IPC-2 (KF). If the IPC-2 criterion is met, the mixture is warmed to 45 – 60C and 25% sodium methoxide solution in methanol is slowly added. The reaction mixture is stirred and held for 30 – 60 minutes at 45 – 55C. The reaction progress is determined by IPC-3 (HPLC). The reaction mixture may be held at a lower temperature during the IPC analysis. If the IPC-3 criterion is met, the process is continued to Unit Operation 1.3. Unit Operation 1.3: Isolation of AP25047 HCI While stirring, the cool reaction mixture is quenched by addition of hydrogen chloride gas. A precipitate forms, and residual hydrogen chloride is removed from the suspension by a nitrogen purge. Tetrahydrofuran (THF) is replaced with toluene by an azeotropic distillation under reduced pressure. The resulting warm slurry is filtered in an agitated filter dryer and the filter cake is triturated and washed with warm toluene. The content of process impurity AP291 16 is determined by IPC-4 (HPLC). If the IPC-4 criterion is met, the wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 35 – 45C (jacket temperature). The drying is monitored by IPC-5 (LOD, gravimetric). If the IPC-5 criterion is met, the crude AP25047 HCI is discharged and packaged in FEP bags in a plastic container. The isolated AP25047 HCI can be held for up to 7 days prior to forward processing. Unit Operation 1.4: Work-up The crude AP25047 HCI solid is charged to a reactor with dichloromethane (DCM) and washed with aqueous ammonia. The aqueous phase is back extracted with DCM for yield recovery purposes and the combined organic phase is washed a second time with aqueous ammonia. The organic layer is then washed with aqueous hydrochloric acid until the aqueous phase reaches a pH of 1-2, as indicated by IPC-6 (pH strips). If the IPC-6 criterion is met, the organic phase is treated with aqueous sodium bicarbonate until the aqueous wash reaches a pH of NLT 7, as indicated by IPC-7 (pH strips). The organic phase is briefly concentrated followed by the addition of fresh dichloromethane. The organic solution is passed through a silica gel pad, which is then rinsed with additional fresh dichloromethane for increased product recovery. Unit Operation 1.5: Crystallization of AP25047 The dichloromethane solution is concentrated under reduced pressure, and the dichloromethane is replaced with 2-propanol by azeotropic distillation under reduced pressure to the targeted final volume range. The resulting suspension is then cooled and further aged with agitation. Unit Operation 1.6: Isolation / Drying The precipitated product is isolated in an agitated filter dryer under a flow of nitrogen, and the filter cake is rinsed with 2-propanol. The wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 45 – 55C (jacket temperature). The drying is monitored by IPC-8 (LOD, gravimetric). If the IPC-8 criterion is met, the product is sampled and packaged into polyethylene bags and placed within a heat sealed mylar coated aluminum foil bag, within an HDPE shipping container (Expected yield range, 65 – 89%).

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; MURRAY, Christopher, K.; ROZAMUS, Leonard, W.; CHABER, John, J.; SHARMA, Pradeep; WO2014/93579; (2014); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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.

Preparation of intermediate H A solution of intermediate G (100 mg, 0.504 mmol), l-iodo-4-(trifluoromethoxy) benzene (CAS [103962-05-6], 145 mg, 0.504 mmol), X-Phos (28.8 mg, 0.06 mmol), Pd(dba)2 (17.4 mg, 0.03 mmol) and t-BuONa (194 mg, 2.02 mmol) in dioxane (4 mL) was irradiated under microwave at 100°C for 1 hour under N2. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (eluent: ethyl acetate / petroleum ether from 0 to 1/1). The desired fractions were collected and concentrated to give intermediate H (100 mg, yield: 55percent).

The synthetic route of 103962-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; GUILLEMONT, Jerome, Emile, Georges; MOTTE, Magali, Madeleine, Simone; RABOISSON, Pierre, Jean-Marie, Bernard; TAHRI, Abdellah; (194 pag.)WO2017/1660; (2017); A1;,
Iodide – Wikipedia,
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