Tag: M.W=300-400

Application of 31827-94-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 31827-94-8 name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

This was a 2-step reaction process. To a solution of (5)-5-(tert-butoxycarbonyl)-5- azaspiro[2.4]heptane-6-carboxylic acid (1.122 kg, 4.65 mol, 1 equiv.) in anhydrous MeCN (10 L) was charged 4′-iodo bromoacetophenone (1.56 kg, 4.80 mol, 1.032 equiv.). The resulting suspension was charged DIPEA (1.215 L, 1.5 equiv.) at the ambient temperature over the period of about 15 min. Upon the completion of the DIPEA addition, the reaction was slightly exothermic (the internal temperature increased up to 25C) and the reaction mass became a clear solution. The reaction was complete within a couple of hours as indicated by HPLC (99+% conversion). It was rotavapped down, solvent swapped to EtOAc (11 L), subsequently washed with water (3 L), then sodium bicarbonate solution (3 L), and finally with brine (2 L). Upon drying over Na2S04, it was rotavapped to dryness and chased with toluene (4 L x 2) to dryness and finally charged toluene (8 L) to give a solution of the coupled intermediate in toluene (about 86% HPLC purity). ESI MS m/z (M+H)+486.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(4-iodophenyl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; TANG, Datong; XU, Guoyou; PENG, Xiaowen; YING, Lu; WANG, Ce; CAO, Hui; LONG, Jiang; KIM, In, Jong; WANG, Guoqiang; QIU, Yao-ling; OR, Yat, Sun; WO2013/59281; (2013); A2;,
Iodide – Wikipedia,
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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 3268-21-1 as follows. Product Details of 3268-21-1

(Step 3) Synthesis of Compound 169; [0096] After 250 mg of 1,4-diiodo-2,3,5,6-tetramethylbenzene (d) (0.648 mmol) was dissolved in 3 ml of 1,2-dimethoxyethane, 0.5 ml of ethanol and 0.5 ml of water were added to the solution. To the solution, 537 mg of potassium carbonate (3.89 mmol) and 350 mg of Boric acid compound (c) (1.943 mmol) were added and 37.4 mg of tetrakis(triphenylphosphine)palladium (0) (0.324 mmol) was added under argon atmosphere. The suspension was refluxed overnight under argon atmosphere. After cooling, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, successively, dried and concentrated. The residue was recrystallized from methanol to obtain Compound 169 (213 mg; 82% yield).

According to the analysis of related databases, 3268-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1354877; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 98-61-3, A common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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: In a typical experiment, the alkene derivative (1.5 mmol), halobenzenesulfonyl chloride derivative (1 mmol), Li2CO3 (0.222 g, 3 mmol), and PdCl2(CH3CN)2 (12.9 mg, 0.05 mmol) were dissolved in 1,4-dioxane (2 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C for 24 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.

The synthetic route of 98-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Skhiri, Aymen; Salem, Ridha Ben; Soule, Jean-Francois; Doucet, Henri; Synthesis; vol. 48; 18; (2016); p. 3097 – 3106;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 63131-30-6,Some common heterocyclic compound, 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, molecular formula is C11H11IO3, 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 A-19Synthesis of 3-(4-iodophenyl)-1-(pyrimidin-2-yl)-1H-pyrazol-5-ol (19)Ethyl 4-iodobenzoylacetate (10 mmol, manufactured by Aldrich) and ethanol (10 mL) were charged in a 100 mL round-bottom flask to which a solution of 2-hydrazinopyrimidine (10 mmol, manufactured by Aldrich) in ethanol (10 mL) was then added. After being stirred at 100 C. for 8 hours, the reaction liquid was cooled at room temperature. The resulting solid was filtered, washed with ethanol and hexane, and then dried under vacuum to afford the title compound.Yield: 49%1H NMR (300 MHz, CDCl3) delta 11.94-11.92 (bs, 1H), 8.79 (d, 2H, J=4.9 Hz), 7.77-7.73 (m, 2H), 7.69-7.65 (m, 2H), 7.27-7.23 (m, 1H), 5.98 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(4-iodophenyl)-3-oxopropanoate, its application will become more common.

Reference:
Patent; EWHA UNIVERSITY- INDUSTRY COLLABORATION FOUNDATION; US2012/220550; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 82777-09-1, name is 2′-Iodo-1,1′:3′,1”-terphenyl, molecular formula is C18H13I, 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. category: iodides-buliding-blocks

General procedure: The outline of our synthetic routes to the 6 compounds listed in Fig. 1 is shown in Scheme 1. They were synthesized by Suzuki-Miyaura coupling of 2,6-dibromodithieno[3,2-b:2?,3?-d]thiophene each with the corresponding boronic acid. Compounds 5 and 7 in Fig. 1 were also synthesized by Suzuki-Miyaura coupling of 3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophene and 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dithieno[3,2-b:2?,3?-d]thiophene with 2?-iodo-1,1?:3?,1?-terphenyl, respectively. The typical procedure is following. A mixture of 2,6-dibromo-dithieno[3,2-b:2?,3?-d]thiophene (174.0 mg, 0.5 mmol), boronic acid of counterpart (1.5 mmol), tetrakis (triphenylphosphine) palladium (81.5 mg, 0.08 mmol) and Cs2CO3 (2.0 mL, 2.0 M in aqueous) in 8 mL solvent of toluene: THF = 1:1 was stirred at reflux temperature for 8 h. All reactions were carried out under nitrogen atmosphere with anhydrous solvents. The mixture was poured into water (30 mL) and extracted with CH2Cl2 (20 mL ¡Á 3). The combined extract was washed with brine (40 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica gel eluted with CHCl3:toluene = 1:1. All compounds were characterized by 1H and 13C NMR and mass spectroscopy.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82777-09-1, its application will become more common.

Reference:
Article; Okada, Shinjiro; Yamada, Kenji; Journal of Molecular Structure; vol. 1037; (2013); p. 256 – 263;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 628-77-3, name is 1,5-Diiodopentane, 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 628-77-3, SDS of cas: 628-77-3

To 1,3-dihydro-1-(2′-trimethylsilylethyl)-2,1-benzisothiazoline 2,2-dioxide (1.3 g, 4.3 mmol) in anhydrous tetrahydrofuran (13 mL) at room temperature was added 1,5-diiodopentane (1.29 mL, 8.6 mmol). The mixture was cooled to -780 C. and lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 17.3 mL, 17 mmol) was added. After 15 min, the reaction mixture was poured into water (50 mL), the layers were separated, and the aqueous phase was extracted with ethyl acetate (3*50 mL). The organic layers were combined, washed with brine (30 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (5% ethyl acetate/hexane) on silica gel gave 1,3-dihydro-3-spirocyclohexyl-1-(2′-trimethylsilylethyl)-2,1-benzisothiazoline 2,2-dioxide (0.8 g, 51%) as an off-white solid. 1H NMR (CDCl3, 300 MHz) delta0.00 (s, 9 H), 0.95 (dd, 2 H, J=8.3, 8.2 Hz), 1.18-2.36 (m, 10 H), 3.72 (dd, 2 H, J=7.8Hz), 8.2, 8.3 Hz), 5.06 (s, 2 H, 7.03 (‘t’, 1 H, J=7.06 (dd, 1 H, J=1, 7.6 Hz), 7.18 (dd, 1 H, J=1.1, 7.6 Hz), 7.28 (dt, 1 H, J=1.3, 7.7 Hz). MS (EI) m/z 367 [M]+

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, 1,5-Diiodopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6339098; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 689260-53-5, 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 689260-53-5 as follows.

2-Bromo-4-iodo1,3-xylene (10 mmol), 5,10-phenothiazine (10 mmol), Cu (20 mmol), under a nitrogen atmosphereK2CO3 (20 mmol) and N,N-dimethylformamide (20 ml) were combined to form a solution.The above mixed solution was evacuated three times with nitrogen, and heated and stirred at 130 C for 24 h. The reaction mixture was filtered through celite and usedWash with dichloromethane (20 ml).The solvent was evaporated under reduced pressure and purified by column chromatography (hexane/dichloromethane 10:1) to give the product 10-(4-bromo-3,5-dimethylphenyl)-phenothiazine S25-1 .

According to the analysis of related databases, 689260-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Zhang Lei; Gao Wei; Zhu Qing; Niu Jinghua; Huang Gaojun; (26 pag.)CN109134520; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, 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. Product Details of 16355-92-3

A mixture of 4-aminoquinaldine 4 kg (25.3 mol),Bis-iodide decane4.3 kg (10.9 mol),Nitrobenzene 9L into the reaction tank,Stir,Heating to 150-160 C,Maintain the temperature reaction for 6 hours,Cooled to room temperature,filter,Respectively, washed twice with methanol (4L each),Filter dry,Washed with 5% hydrochloric acid solution twice,Washed with water to pH 6,Filter dry,And then rinse with the amount of methanol once,Filter dry,60-70 drying,Get grayish yellow powder,That is, decane 1,10-bis (4-aminoquinaldin iodide) salt (referred to as quaternary ammonium iodide).The yield of quinacridine was 3.64 kg,Yield of about 47%.After testing,The quaternary ammonium iodide has a melting point of 300-308 C.

The synthetic route of 1,10-Diiododecane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; (12 pag.)CN106854179; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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.

[153] The intermediate 4-N-(2-Dimethylaminoethyl)-N-(2-bromo-4,5- dimethoxybenzoyl)amine-6,7-methylenedioxycinnoline (D) was prepared as follows:[ 154] a. 4-N-(2-Dimethylaminoethyl)-N-(2-bromo-4,5-dimethoxybenzoyl)amine-6,7-methylenedioxycinnoline (D). A 2.0M solution of oxalyl chloride in methylene chloride (5 mL, 10.0 mmol) was added to a solution of 2-iodo-4,5-dimethoxybenzoic acid (1.50g, 4.8mmol) in anhydrous methylene chloride (45 mL) and the stirred mixture was refiuxed for 2 hours. The mixture was then concentrated to dryness under reduced pressure. To this residue was added a solution of N-(2- Dimethylaminoethyl)-4-amino-6,7-methylenedioxycinnoline (3, 1.0 g, 3.84 mmol), and triethylamine (760 mg 7.52 mmol) in methylene chloride (60 mL) and the resulting mixture was stirred at reflux under nitrogen for 4 hours, then cooled to room temperature; stirring was continued overnight. The reaction mix was washed with a saturated solution of sodium bicarbonate (3 x 40 mL), dried (anhydrous MgS04), and concentrated in vacuo. The crude material was chromatographed over silica using 90: 10 chloroform:methanol to give compound D (1.59 g), in 75 % yield; 1H NMR (CDCI3) delta 2.27(s, 6H), 2.53(m, 2H), 3.43(s, 3H), 3.75(s, 3H), 3.97(m, 1H), 4.44(m, 1H), 6.24(s, 1H), 6.25(s, 1H), 6.43(s, 1H), 7.02(s, 1H), 7.43(s, 1H), 7.68(s, 1H), 9.18(s, 1H); 13C NMR (CDC13) delta 45.5, 47.1, 55.7, 56.1, 56.7, 82.8, 96.7, 102.9, 105.4, 110.6, 121.9, 123.2, 133.1, 136.0, 144.8, 148.2, 149.9, 150.9, 151.7, 152.4, 169.8; HRMS calcd for C22H2305N4IH: 551.0791; found 551.0795.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4,5-dimethoxybenzoic acid, its application will become more common.

Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly, A.; SCHMID, Steven, M.; WO2012/15901; (2012); 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. 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 34270-90-1

A stirred solution of Intermediate 71 (0.8 g, 2.42 mmol) and 1-iodo-2-(2-iodoethoxy)ethane (0.38 mL, 2.67 mmol) in anhydrous DMF (16 mL) was cooled to -l5C30 and purged with nitrogen for 5 minutes, then caesium carbonate (3.16 g, 9.69 mmol) wasadded. The reaction mixture was stirred for 2 h, with warming to 20C. Water (30 mL)was added and the aqueous layer was extracted with tert-buty1 methyl ether (3 x 30 mL).The combined organic layers were washed with water (2 x 30 mL) and brine (30 mL), then dried over sodium sulfate, filtered and concentrated. The resulting crude materialwas purified by flash column chromatography, using a gradient of tert-buty1 methyl etherin heptane (0-15%), to afford the title compound (927.9 mg, 86%) as a yellow solid. DH(500 MHz, CDCb) 7.90 (d, J 1.3 Hz, 1H), 7.06 (dd, J9.1, 1.6 Hz, 1H), 4.26 (t, J 11.8 Hz,5 2H), 3.89 (dd, J 11.9, 3.6 Hz, 2H), 2.45-2.33 (m, 2H), 1.75-1.69 (m, 2H), 1.65 (s, 9H).HPLC-MS (method 5): [M+H-BOC]+ m/z 300.0, 302.0, RT 2.11 minutes.

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com