Tag: M.W=200-300

Application of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip) belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 11 (65 mg, 0.1 mmol), 1,3-diiodopropane (88.8 mg, 0.3 mmol) was added to an 8 mL vial.DIPEA (diisopropylethylamine, 20 uL), acetonitrile (150 uL), and the reaction mixture was reacted at 80 C for 12 hours.The reaction solution was drained, washed with DCM, washed with saturated aqueousThe solid was washed with diethyl ether to give a white solid compound 12 (40 mg, yield = 38%)

The synthetic route of 1,3-Diiodopropane(stabilized with Copper chip) has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 20691-72-9, name is 4-Iodo-2-nitroaniline, 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 20691-72-9, Quality Control of 4-Iodo-2-nitroaniline

Method a To a solution of diphosgene (4.1 mL, 34.1 mmol) in EtOAc (40 mL) at 0 C. was added a solution of the 4-iodo-2-nitroaniline (45.5 mmol) in EtOAc (200-500 mL), and the mixture was heated to reflux for 18 h. The solvent was removed in vacuum to leave a brown solid, which was triturated with hot hexane (200 mL). The solid material was filtered off and the filtrate was concentrated under reduced pressure to leave the pure 4-iodo-2-nitrophenylisocyanate as a yellow solid.

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6509328; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 83863-33-6, A common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

A solution of 5-iodo-2-methylaniline (1g, 42.91mmol) and 2-tert butyldicarbonate (1.03g, 47.19 mmol) in THF (10 ml) was stirred at reflux temperature for 2 hours. Solvent was then removed in vacuo, the residue dissolved in ethyl acetate and this solution was washed successively with 1M citric acid solution and brine. The organic phase was dried over MgSO4 and concentrated in vacuo. The resultant yellow-white solid was crystallized from hexane to give white solid 2 (1.22 g, 85.3%).

The synthetic route of 83863-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Raju, Gheevarghese; Capo, Joseph; Lichtenstein, Bruce R.; Cerda, Jose F.; Koder, Ronald L.; Tetrahedron Letters; vol. 53; 10; (2012); p. 1201 – 1203;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 3032-81-3, 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. 3032-81-3 name is 1,3-Dichloro-5-iodobenzene, 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.

8-Mercaptoadenine (3.6 mmol), neocuproine hydrate (0.36 mmol), Cul (0.36 mmol), NaO-?-Bu (7.2 mmol), 3,5-dichloro-iodobenzene (10.8 mmol), and anhydrous DMF (24 mL) were added to a round bottom flask flushed with nitrogen. The flask was sealed with Teflon tape and heated at 1 10 °C with stirring for 24-36 h under nitrogen. Solvent was removed under reduced pressure and the resulting residue was chromatographed (CH2Cl2:MeOH:AcOH, 20: 1 :0.5) to yield 15 as a yellow solid in 44 percent yield. -NMR (400 MHz, DMSO-i/6) delta 13.49 (IH, br s), 8.13 (IH, s), 7.59 (IH, s), 7.47 (2H, s), 7.36 (2H, br s); MS (ESI): m/z 312.1 [M + H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dichloro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 97456-81-0, name is 1-Bromo-3-iodo-2-methylbenzene, 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 97456-81-0, Computed Properties of C7H6BrI

Step 3: preparation of (E)-methyl 4-(3-bromo-2-methylstyryl)-5-chloro-2-methoxybenzoate 1-Bromo-3-iodo-2-methylbenzene (616 mg, 2.07 mmol), methyl 5-chloro-2-methoxy-4-vinylbenzoate (470 mg, 2.07 mmol), Pd(Oac)2 (47 mg, 0.21 mmol), tri-o-tolylphosphine (126 mg, 0.415 mmol), Hunig’s Base (724 mul, 4.15 mmol), tetrabutylammonium chloride (576 mg, 2.07 mmol) were combined under N2 in acetonitrile (21 ml) at rt and warmed to 70 C. The reaction was stirred for 6 hr and then was concentrated, adsorbed onto diatomaceous earth (Celite) and was purified on silica gel (Biotage, 0-50% EtOAc/hexanes gradient over 10 CVs) to afford (E)-methyl 4-(3-bromo-2-methylstyryl)-5-chloro-2-methoxybenzoate (550 mg, 67% yield) as a yellow solid consistent by LCMS: M+H=396.80, Retention time=1.625 min, and NMR: 1H NMR (500 MHz, CHLOROFORM-d) delta 7.88 (s, 1H), 7.55 (t, J=8.1 Hz, 2H), 7.37-7.35 (m, 1H), 7.29 (s, 1H), 7.21 (s, 1H), 7.11 (t, J=7.9 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H), 2.54 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-iodo-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, KAP-SUN; Connolly, Timothy P.; Frennesson, David B.; Grant-Young, Katharine A.; Hewawasam, Piyasena; Langley, David R.; Meng, Zhaoxing; Mull, Eric; Parcella, Kyle E.; Saulnier, Mark George; Sun, Li-Qiang; Wang, Alan Xiangdong; Xu, Ningning; Zhu, Juliang; Scola, Paul Michael; (511 pag.)US2017/107202; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 108078-14-4,Some common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, molecular formula is C8H7IO2, 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 131; 122 Dioxanel-d-Iodo-S-methyl-benzoylaminoHndan-l-carboxylic Acid Ethyl EsterA 10OmL round bottom flask is charged with 2-Iodo-3-methylbenzoic Acid (1.92g, 7.3 lmmol) and dry DCM (25mL). A stirring bar is added and stirring initiated. After 5min, HTBU (2.37g, 7.3 lmmol) is added. After 5min, the 2-amino-indane-2-carboxylic Acid Ethyl Ester (1.5Og, 7.31mmoles) is added followed by DIPEA (3.2mL, 18.37mmol). The reaction is allowed to stir for 118 hours. Analysis by tic of the reaction mixture (silica, 15% iPrOH/Dischloromethane) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (70 mL). This is washed with dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 x 3OmL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of white solid. This material is dissolved in DCM (15mL). This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAC in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active elutant were collected. Fractions 10 through 15 are combined and evaporated in vacuo to constant weight to give 2-(2-iodo-3-methyl- benzoylamino)-indan-2-carboxylic acid ethyl ester 1.04g of white solid.EXAMPLE 175; 149 l-d-Iodo-S-methyl-benzoylaminoHndane-l-carboxylic acid ethyl ester (175):A 10OmL round bottom flask is charged with 2-iodo-3-methylbenzoic acid (1.92g, 7.31mmol) and dry DCM (25mL). A stirring bar is added and stirring is initiated. After 5min, the HBTU (2.37g, 7.31mmol) is added. After 5min, the 2-amino-indane-2-carboxylic acid ethyl ester(1.5g, 7.31mmol) is added followed by N,N-diisopropylethyl-amine (3.2mL, 18.37mmol). The reaction is allowed to stir for 118h. Analysis by tic of the reaction mixture (silica, 15% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (7OmL). This is washed dilute aqueous HCl (3%, 2 x 3OmL), saturated aqueous NaHCO3 (2 X 3OmL) and brine (3OmL), dried over MgSO4, filtered and evaporated in vacuo to provide 2.04g of a white solid. This material is dissolved in 15mL of DCM. This material is purified utilizing an ISCO Companion with a 4Og cartridge of silica. The gradient is 10 % EtOAc in heptanes over 4 column volumes followed by a linear gradient to 50% EtOAc over 10 column volumes. 27mL fractions of UV active eluent are collected. Fractions 10 through 15 are combined and evaporated in vacuo. Pumping to constant weight gives 1.04g a white solid material.1H NMR (300 MHz, DMSO-d6): delta 1.20 (t, 3 H), 2.39 (s, 3 H), 3.52 (dd, 4H), 4.15 (q, 2H), 6.79 (d, IH), 6.97 (d, IH), 7.16 – 7.24 (m, 4H), 7.28 – 7.38 (m, 2H), 9.15 (s, IH). LC/MS m/z = 450.

The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 10297-05-9,Some common heterocyclic compound, 10297-05-9, name is 1-Chloro-4-iodobutane, molecular formula is C4H8ClI, 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 23: 2-[5-Chloro-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene Under an argon atmosphere and at -78°C, n-butyl lithium (a 1.57M hexane solution, 3.52 ml) was added to a dimethoxyethane solution (30 ml) of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (1.52 g, 5.02 mmol) obtained in Example 5.. The temperature of the reaction mixture was elevated to room temperature, at which stirring was conducted for 15 minutes.. After cooling the reaction mixture to -78°C, 4-chloro-1-iodobutane (672 mul, 5.52 mmol) was added thereto and the mixture was stirred at room temperature for 24 hours.. A saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether.. The extracts were combined, washed successively with water, a saturated aqueous solution of sodium thiosulfate and brine, dried over MgSO4, and then distilled under reduced pressure to remove the solvent.. The residue thus obtained was recrystallized from hexane, whereby the title compound (1.64 g, 83percent) was obtained as colorless needle crystals. IR (ATR) nu: 2945, 1583, 1495, 1475, 1311, 1277, 1230, 1149, 1142, 1082, 1014, 872, 822, 793, 752, 708, 629, 557, 532, 465 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.33-1.48(2H,m), 1.72-1.87(2H,m), 2.08-2.18(1H,m), 2.43-2.52(1H,m), 3.44-3.53(2H,m), 4.52(1H,ddd,J=11.5,3.9,1.2Hz), 6.84(1H,td,J=9.0,4.4Hz), 6.96-7.02(1H,m), 7.23-7.28(1H,m), 7.39(2H,d,J=8.8Hz), 7.53(2H,d,J=8.8Hz). MS (m/z): 393 (M++H). Elemental Analysis for C17H16Cl2F2O2S Calculated: C 51.92percent; H 4.10percent; Cl 18.03percent; F 9.66percent; S 8.15percent. Found: C 51.33percent; H 4.07percent; Cl 17.64percent; F 9.72percent; S 8.25percent.

The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); 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 202865-85-8 as follows. Recommanded Product: 1-Bromo-4-iodo-2-methylbenzene

General procedure: General Procedure A: (0312) A mixture of an arylbromide or aryliodide (1 mmol), an arylboronic acid, aryldioxaborolane or bis(pinacolato)diboron (1.5 mmol), a palladium catalyst (0.1 mmol) and K2CO3 (2-3 mmol) was placed in a reaction vessel which was then thoroughly purged with argon. Dioxane (3 mL) and water (1.5 mL) were added, and the mixture was stirred at 80-95 C. for 1 to 4 h. After cooling to rt, the mixture was poured into EtOAc/H2O (1:1, 10 mL) and the aqueous layer was extracted with EtOAc (5 mL×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (EtOAc/heptanes) afforded the desired biaryl product.

According to the analysis of related databases, 202865-85-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20691-72-9, name is 4-Iodo-2-nitroaniline, 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. Quality Control of 4-Iodo-2-nitroaniline

4-Iodo-2-nitroaniline (35.2 g, 0.133 mol) was added in batches via an open funnel over 25 mm to a heated (65 0C) mixture of SnCl2JH2O (106.86 g, 0.465 mol) and 12 N HCl (200 ml). An additional 12N HCl (30 ml) was added and the reaction mixture was heated at 65 0C for an additional 1 h, and stirred at room temperature for 1 h. It was placed in a refrigerator for 15 h, and the precipitate was filtered. The resultant solid was transferred into a flask containing water (210 ml), cooled (ice/water), and a solution of NaOH (aq) (35 g in 70 ml of water) was added to it over 10 min with stirring. The cooling bath was removed, and vigorous stirring was continued for 45 min. The mixture was filtered and the solid was washed with water and dried in vacuo to provide iodide M47a as a tan solid (25.4 g). The product was used in the next step without further purification. 1H NMR (DMSO-dg, delta – 2.5 ppm, 500 MHz): 6.79 (d, J – 2,1H), 6.63 (dd, J = 1.9, 8.1, IH), 6.31 (d, J = 8.1, IH), 4.65 (br s, 2H), 4.59 (br s, 2H). LC/MS: Anal. Calcd. for [M+H]+ C6H8IN2: 234.97; found: 234.9.

The synthetic route of 20691-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; GOOD, Andrew, C.; GOODRICH, Jason; KAKARLA, Ramesh; LI, Guo; LOPEZ, Omar, D.; NGUYEN, Van, N.; KAPUR, Jayne; QIU, Yuping; ROMINE, Jeffrey, Lee; ST. LAURENT, Denis, R.; SERRANO-WU, Michael; SNYDER, Lawrence, B.; YANG, Fukang; WO2010/17401; (2010); 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. 34883-46-0, name is 1-Iodo-2-phenoxybenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H9IO

Intermediate Bn (1.0 eq) was dissolved in 120 mL of anhydrous THF (0.4M), and cooled to -78 C. n-Butyllithium (n-BuLi)(2.5 M, 1.0 eq) was slowly added to the above cooled solution, and the reaction mass was stirred for 1 h. After 1 h of stirring, Intermediate An (0.7 eq) was added to the reaction solution and stirred for additional 3 h at normal temperature. After the completion of the reaction, it was quenched by saturated solution of ammonium chloride, and extracted with organic solvent. The organic layer was separated, concentrated, and recrystallized with petroleum ether to obtain a white solid product. The white solid product was analyzed by FD-MS, and the result was listed in Table 3-1. The chemical structures of Intermediates Cn-1 were listed in Table 3-1

The synthetic route of 34883-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NICHEM FINE TECHNOLOGY CO., LTD.; WU, Hui-Ling; LIAO, Liang-Di; SHIEH, Shwu-Ju; CHEN, Chi-Chung; (145 pag.)US2018/155312; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com