Author: Jessica.F

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

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

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

Application of 3819-88-3,Some common heterocyclic compound, 3819-88-3, name is 1-Fluoro-3-iodo-5-nitrobenzene, molecular formula is C6H3FINO2, 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 solution of 1.0 eq IA in dry DMF (0.37 M) was added Zn(CN)2 (0.92 eq) and Pd(PPli3)4 (0.058 eq). The reaction mixture was purged with nitrogen and heated to 800C overnight. An additional 0.023 eq of Pd(PPh3)4 was then added and the reaction was heated for another 6 hrs. The reaction mixture was then cooled to RT, diluted with 15 volumes of EtOAc (based on IA) and the organic layer was washed 3 times with water and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by chromatography over silica gel using 10% Et2O/hexane as the eluant provided IB as a solid (90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-3-iodo-5-nitrobenzene, its application will become more common.

Reference:
Patent; CYTOKINETICS, INC.; WO2007/70626; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 75581-11-2, 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. 75581-11-2, name is 4-Iodo-1-methoxy-2-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00359] In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (21 mg; 0.026 mmol) and triethylamine (0.34 ml; 2.44 mmol) in dioxane (2.5 ml; dried over 4 A sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (0.19 ml; 1.31 mmol) was added followed by 1-iodo-4-methoxy-3-methylbenzene (215 mg; 0.867 mmol) in dioxane (2.5 ml; dried over 4 A sieves) and the reaction mixture was stirred at 80 C. GC analysis after 18 hours showed a single new peak at 11.4 minutes which was identified by GC/MS as the desired arylborate compound.

The synthetic route of 4-Iodo-1-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 450412-28-9, 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. 450412-28-9, name is 1-Bromo-3-chloro-2-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate A1 (95.2 g, 0.29 mol),1-Bromo-3-chloro-2-iodobenzene (109.1 g, 0.34 mol),Copper Iododide (54.5 g, 0.29 mol) and K3PO4 (182.1 g, 0.86 mol) were placed in dimethylacetamide (950 mL) and the mixture was refluxed and stirred.After the reaction was completed, the reaction solution was cooled to room temperature and then copper was removed by filtration. The solution in which the product was dissolved was reduced in pressure to remove all of the solvent. Then, the solution was completely dissolved in CHCl 3 and washed with water. The solvent was then removed under reduced pressure, and the resulting product was purified by column chromatography to obtain 132.1 g of intermediate A2 (yield: 88% .

The synthetic route of 1-Bromo-3-chloro-2-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Lee Jeong-ha; Park Tae-yun; Lee Dong-hun; Kim Min-jun; (39 pag.)KR2018/40100; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 55406-53-6, name is 3-Iodoprop-2-yn-1-yl butylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 55406-53-6

EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of IPBC was determined by means of HPLC at the beginning and after two weeks.

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; Uhr, Hermann; US2009/36555; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 1878-69-9,Some common heterocyclic compound, 1878-69-9, name is 2-(3-Iodophenyl)acetic 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.

To a 125 mL round-bottom flask in a 0 C ice bath was added 3-iodobenoic acid (5.0 g, 23 mmol), EDCI (5.0 g, 26 mmol), DCM (50 mL) and allowed to stir for 10 min. To the stirred solution was added DMAP (0.3 mg, 2.3 mmol) and methanol (1.1 mL) and the reaction allowed to stir overnight. Disappearance of SM was monitored by HPLC. Reaction mixture was diluted with DCM, washed with 1 N HCI, dried with magnesium sulfate, and concentrated in vacuo. Required column chromatography (10: 1 Hex/EtOAc) to isolate product (4.56 g, 87%); LC rt = 3.77 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Iodophenyl)acetic acid, its application will become more common.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, molecular formula is C8H6BrIO, 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. Quality Control of 2-Bromo-1-(4-iodophenyl)ethanone

General procedure: The appropriate carbonyl compound (50 mmol) was dissolved in 50 mL of ethanol and magnetically stirred with an equimolar quantity of thiosemicarbazide for 24 h at room temperature with catalytic amounts of acetic acid. The desired thiosemicarbazone precipitated from reaction mixture, was filtered, crystallized from suitable solvent, and dried. Equimolar quantities of 4-iodo-acetophenone and bromine, both dissolved in chloroform, were stirred for 4 h at room temperature until the presence of HBr disappeared. The solution was evaporated under vacuum and the obtained pale yellow solid was washed with petroleum ether to give alpha-bromo-4-iodo-acetophenone in good yield (94%). Equimolar amounts of the prepared thiosemicarbazone (50 mmol) and alpha-bromo-4-iodo-acetophenone (50 mmol), both suspended in 50 mL of ethanol, were reacted at room temperature under magnetic stirring for 10 h. The precipitate was filtered and purified by chromatography to give compounds 1-25 in high yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31827-94-8, its application will become more common.

Reference:
Article; Secci, Daniela; Bizzarri, Bruna; Bolasco, Adriana; Carradori, Simone; D’Ascenzio, Melissa; Rivanera, Daniela; Mari, Emanuela; Polletta, Lucia; Zicari, Alessandra; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 246 – 253;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 364-12-5, name is 5-Bromo-2-iodobenzotrifluoride, A new synthetic method of this compound is introduced below., name: 5-Bromo-2-iodobenzotrifluoride

A vial containing 4-bromo-l-iodo-2-(trifluoromethyl)benzene was charged with potassium phosphate (0.130 g, 0.614 mmol), followed by a solution of N-(2,4- dimethoxybenzyl)-l-methyl-3-(4,4,5,5-tetramethyl- 1,3, 2-dioxaborolan-2-yl)-N-( 1 ,2,4- thiadiazol-5-yl)-lH-indole-6-sulfonamide (Intermediate H) (0.100 g, 0.175 mmol) and PdCl2(dppf)-CH2Cl2 (0.014 g, 0.018 mmol) in 1 mL of DMF. The vial was sealed and placed in a shaker block. The block was shaken for three hours at 85 C. The solution was filtered, washed with DMF and concentrated. The resulting solid was treated with a solution of TFA (0.270 mL, 3.51 mmol) in 1 mL of DCM. The vial was shaken at room temperature for two hours. The solution was concentrated and purified via reverse phase HPLC (8 min. gradient elution 15 to 75% ACN/H20, 0.1% TFA modifier) to afford 3-(4- bromo-2-(trifluoromethyl)phenyl)-l-methyl-N-(l,2,4-thiadiazol-5-yl)-lH-indole-6- sulfonamide as an off-white solid.

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; DINEEN, Thomas; MARX, Isaac, E.; NGUYEN, Hanh, Nho; WEISS, Matthew; AMGEN INC.; WO2013/25883; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com