Author: Jessica.F

Reference of 619-58-9, A common heterocyclic compound, 619-58-9, name is 4-Iodobenzoic acid, molecular formula is C7H5IO2, 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 solution of 4-iodobenzoic acid (6 g, 24.19 mmol) in DCM (300 mL) was added 1,1-carbonyldiimidazole (4.3 15 g, 26.61 mmol) at0C. After being stirred at rt for 2h, hydrazine monohydrate (7.26 g, 145.15 mmol) was added and the mixture was stirred at ft for 5h. The mixture was then concentrated under reduced pressure followed by the addition of water to precipitate out the product. The product was collected by filtration and dried under reduced pressure to afford 15-1 (5.2 g, 82%) as an off white solid. LCMS: 263.05 [M+Hjt

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; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter, Qinhua; KAHRAMAN, Mehmet; BUNKER, Kevin, Duane; (194 pag.)WO2018/67512; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 124700-41-0, 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. 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Fluoro-5-iodobenzoic acid (6.60 g, 24.81 mmol) was dissolved in chloroform (70 ml) and oxalyl chloride (4.30 ml, 49.29 mmol) and dimethylformamide (catalytic amount) were added. The mixture was stirred at room temperature for 3 hrs. The reaction solution was concentrated under reduced pressure and chloroform (35 ml), was added to dissolve the residue. The obtained solution was added dropwise to a solution of ethyl 3,3-dimethylaminoacrylate (4.26 g, 29.75 mmol) and triethylamine (5.19 ml, 37.24 mmol) in chloroform (35 ml), and the mixture was stirred at room temperature for 15 hrs. Water was added to partition the reaction solution, and the organic layer was washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel chromatography (ethyl acetate_hexane=1:2 to 1:1) to give an object product (6.40 g, yield 66%) of a mixture of E form and Z form as an orange solid.1H NMR(CDCl3 400MHz) (delta) ppm: 0.94 (3H, t, J=7.2Hz), 2.88 (3H, brs), 3.31 (3H, brs), 3.97 (2H, q), 6.78 (1H, dd, J=8.4, 10.0Hz), 7.65-7.67 (1H, m), 7.78(1H, s), 7,85 (1H, brs) MS (ESI) : M+ 392

The synthetic route of 2-Fluoro-5-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; EP1564210; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 460-37-7, The chemical industry reduces the impact on the environment during synthesis 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, I believe this compound will play a more active role in future production and life.

5-Ch[oro-N-(piperidin-4-y[)pyrazine-2-carboxamide trifluoroacetic acid salt[Intermediate 68] (722 mg, 3.00 mmol, 1 .0 eq), and potassium carbonate (2.07 g, 15.0 mmol, 5.0 eq) were suspended in 33 mL acetonitrile. Then, 1,1,1- trifluoro-3-iodopropane [CAS RN: 460-37-7] (1.01 g, 4.50 mmol, 1.5 eq) was added and the reaction mixture was heated to 70C for 4 h. On cooling, the reaction mixture was diluted with water and extracted withdichloromethane/isopropanol (4/1) (2x). The combined organic phases were washed with brine. Phase separation was conducted by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 50 g SNAP cartridge:dichloromethane -> dichloromethane/ethanol 95/5) to give 900 mg (41% yield oftheory) of the title compound.UPLC-MS (Method 1): R = 0.58 mm; MS (ESI0): m/z = 337 [M+H].

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, 1,1,1-Trifluoro-3-iodopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 624-75-9, 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 624-75-9 as follows.

e) To a solution of 7-benzyloxymethyl-8-(4-hydroxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione (1 g, 2.2 mmol) in tetrahydrofuran (20 ml) was added potassium t-butoxide (0.28 g, 2.4 mmol), and the mixture stirred for 30 minutes at room temperature. Iodoacetonitrile (0.38 g, 2.23 mmol) was then added, and the mixture stirred for 16 hours at room temperature. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and passed through a silica gel plug, to provide 7-benzyloxymethyl-8-(4-cyanomethoxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione, a compound of formula (7)

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CV Therapeutics, Inc.; US6977300; (2005); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 35674-27-2, A common heterocyclic compound, 35674-27-2, name is 4-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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.

Example 1 Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Methanol/Sulfuric Acid To a solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) cooled to 0 C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly. The reaction mixture is warmed to room temperature and then refluxed (?70 C.) for 8 hours. After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered. The filtrate is evaporated under reduced pressure. To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml*2). The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered. After evaporating the solvent under reduced pressure, 4-iodo-3-nitro-benzoic acid methyl ester is obtained as a yellow solid (2.67 g, 85% yield, 98% HPLC).

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; DIVI’S LABORATORIES LIMITED; Divi, Murali Krishna Prasad; Rao, Mysore Aswatha Narayana; Rajuri, Venkataramana; US2013/172618; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 628-77-3,Some common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, molecular formula is C5H10I2, 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 141:(S)-1 -(1 -(4-bromophenyl)ethyl)piperidineTo a solution of (S)-i -(4-bromophenyl)ethanamine (1 .439 mL, 10.00 mmol) in DMF, were added potassium carbonate (4.14 g, 30.0 mmol) and 1,5-di- iodopentane (2.98 mL, 19.99 mmol). The reaction mixture was heated at 90 C in DMF for 16 h. The reaction mixture was concentrated, the product was extractedwith ethyl acetate and purification was done using column chromatography (silica gel, 30 % CHCI3 in DCM) to yield the title compound.Yield: 2 g (74.6%); 1H NMR (DMSO-d6, 300 MHz): 6 7.4 – 7.6 (d, 2H), 7.1 – 7.3 (d, 2H), 3.2 – 3.3 (m, 1 H), 2.1 – 2.4 (m, 4H), 1.4 – 1.5 (m, 4H), 1.3 – 1.4 (m,2H), 1.1 – 1.2 (m, 3H); MS (ESl+): m/z 269 [M+H] HPLC Purity: 96.30 %.

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

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); 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. 167479-01-8, name is tert-Butyl (3-iodopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 167479-01-8

Part C; A solution of 4-amino-2-ethoxymethyl-l -isopropylamino-lH-imidazo[4,5- c]quinolin-7-ol (0.11 g, 0.35 mmol) in 10 mL of N,N-dimethylformamide was placed under an atmosphere of nitrogen and was treated with cesium carbonate (0.23 g, 0.70 mmol). After 5 min of stirring the mixture was treated with tert-butyl 3- iodopropylcarbamate (0.12 g, 0.35 mmol) and heated to 65 0C. After 60 h, the reaction mixture was cooled to ambient temperature and then poured into 100 mL of ice water which resulted in a cloudy suspension. The mixture was extracted with CHCl3 (5 X 25 mL). The combined organic extracts were then washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan oil. Chromatography (95:5 CHC13:(80: 18:2 CHCl3 :MeOH:NH4OH) gradient to 1 : 1 gave 0.040 g of tert-butyl [3-(4-amino-2-ethoxymethyl-l-isopropylamino-lH-imidazo[4,5-c]quinolin- 7-yloxy)propyl]carbamate as a light tan solid. LC/MS (APCI) m/z 473 (M+Eta)+.

According to the analysis of related databases, 167479-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/28451; (2006); 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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 128140-82-9

Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

According to the analysis of related databases, 128140-82-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2007/72925; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 4387-36-4, 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. 4387-36-4, name is 2-Iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An oven-dried resealable Schlenk tube were charged with CuI (10 mol percent), 1,10-phenanthroline (20percent mol), Cs2CO3 (1.4-2.0 mmol),aryl iodide (1.0 mmol).The Schlenk tube was evacuated and back-filled with argon and 2-trimethylsilyl alcohol (3mmol) and toluene (0.5 ml) were added. Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 110°C for 14 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 x 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product.

The synthetic route of 2-Iodobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dibakar, Mullick; Prakash, Anjanappa; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam; Tetrahedron Letters; vol. 52; 41; (2011); p. 5338 – 5341;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, 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 847685-01-2, Recommanded Product: 847685-01-2

General procedure for the synthesis of lH-indole-2-carboxylic acid AA mixture of the appropriate ort/zo-iodoaniline (5 mmol), pyruvic acid (1.04 mL, 15 mmol), DABCO (1.683 g, 15 mmol) and Pd(OAc)2 (56 mg, 0.25 mmol) in dry DMF (15 mL) was degassed 3 times and then was stirred at 105C for 16 h. The mixture was cooled to room temperature, neutralized with 10% aqueous hydrochloric acid and extracted with EtOAc (3×15 mL). The combined organic phases were washed with brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography using 95/5 EtOAc/MeOH and recrystallized from EtOH to yield the IH- indole-2-carboxylic acid.5,6-difluoro-l//-indoIe-2-carboxylic acid Al Yield = 43%, pale grey powder. Mp = 292-293C. NMR (600 MHz, DMSO-c/6): delta 13.11 (bs, 1H), 11.97 (bs, 1H), 7.66 (dd, J = 10.8 Hz, 8.4 Hz, 1H), 7.33 (dd, J = 10.8 Hz, 6.6 Hz, 1H), 7.09 (d, J= 1.2 Hz, 1H). 13C NMR (150 MHz, CDC13 + DMSO-^): delta 162.5, 148.9 (dd, J = 242 Hz, 16 Hz), 146.2 (dd, J = 237 Hz, 16 Hz), 132.3 (d, J – 11 Hz), 129.5 (d, J = 4 Hz), 121.8 (d, J= 8 Hz), 107.4, 107.3 (d, J= 19 Hz), 99.5 (d, J= 22 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Difluoro-2-iodoaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF BRITISH COLUMBIA; SIMON FRASER UNIVERSITY; REINER, Neil E.; FINLAY, Barton B.; BRUNHAM, Robert C.; TCHERKASSOV, Artem; FOSTER, Leonard J.; MCMASTER, William R.; SEE, Raymond H.; ZORAGHI, Roya; HSING, Michael M. K.; BYLER, Kendall G.; AXERIO-CILIES, Peter J.; BAN, Fuqiang; KUMAR, Nag; MOREAU, Anne; LABRIERE, Christophe; YOUNG, Robert N.; WO2012/51708; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com