Month: September 2021

These common heterocyclic compound, 640280-28-0, name is 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, 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. Safety of 1-Bromo-2-iodo-4-(trifluoromethyl)benzene

A vial was charged with N-(2,4-dimethoxybenzyl)-l-methyl-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-N-(l,2,4-thiadiazol-5-yl)-lH-indole-6-sulfonamide (.500 g, 0.876 mmol), 2-bromo-l-iodo-4-(trifluoromethyl)benzene (0.769 g, 2.191 mmol), potassium phosphate (0.651 g, 3.07 mmol), and PdCi2(dppf)-CH2Ci2 (0.072 g, 0.088 mmol). DMF (5.84 ml), and the vial was flushed with argon, sealed, and stirred at 60 C for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (silica gel, gradient elution 0 to 100% EtOAc:Hexanes) to afford 3-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4- dimethoxybenzyl)-l-methyl-N-(l ,2,4-thiadiazol-5-yl)-lH-indole-6-sulfonamide (.255 g, 0.382 mmol, 43.6 % yield) as an off-white solid, m/z (ESI) 667.0 (M+H)+.

The synthetic route of 1-Bromo-2-iodo-4-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 2468-56-6, A common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, 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: 4.2.1 Synthesis of ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate (3a). To a solution of 2 (0.20 g, 0.99 mmol) in anhydrous DMF (3 mL) under N2 at 0 C was added NaH (0.044 g, 1.09 mmol). The mixture was warmed to rt and stirred for 30 min. After cooling back to 0 C, ethyl bromoacetate (0.12 mL, 1.09 mmol) was added and the mixture stirred at rt for 2 h. The reaction was quenched with saturated NH4Cl (10 mL) and the product extracted into ethyl acetate (3*30 mL). The combined organic extract was dried (Na2SO4) and the solvent removed in vacuo. Excess DMF was removed by Kugelrohr distillation. The crude product was purified by radial chromatography (hexane/ethyl acetate gradient) to give ester 3a (0.26 g, 93%) as a 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:
Article; Gibson, Sarah; Fernando, Rasika; Jacobs, Hollie K.; Gopalan, Aravamudan S.; Tetrahedron; vol. 71; 49; (2015); p. 9271 – 9281;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 103440-52-4, A common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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.

In a dry Schlenk Tube at RT under nitrogen are successively charged 2-iodo-5-methylbenzoic acid methyl ester (13.765 mmol, 1 eq), Cul (2.753 mmol, 0.2 eq), CsF (27.529 mmol, 2 eq), 2-tributylstannylpyridine (20.647 mmol, 1.5 eq), Pd(PPh3)4 (1.376 mmol, 0.1 eq) and DMF (60 mL). The resulting suspension is stirred at 90C overnight. The obtained reaction mixture is diluted with EtOAc and filtered through a short pad of Celite. A solution of sat. aq. NaHC03 is then added to the filtrate and the aq. phase extracted with EtOAc (3 times). The combined organic layers are washed with H20 and brine, dried over Na2S04, filtered and concentrated under reduced pressure. Purification is achieved by FC (EtOAc/Heptane 1 :4 to 3:7) to give methyl 5-methyl-2-(pyridin-2-yl)benzoate as a brown oil. LC-MS (conditions B): tR = 0.67 min, [M + 1]+ = 228.07.

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; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2013/50938; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1878-94-0, Name is 2-(4-Iodophenoxy)acetic acid, 1878-94-0, 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.

3-[2-(4-iodo-phenoxy)acetyl-amino]-benzamideTo (4-iodo-phenoxy)-acetic acid (83.5 mg, 0.3 mmol), 3-aminobe?zamide (61.3 mg, 0.45 mmol), N- (3-dimethylaminopropyl)-N-ethyl carbodmideHCl (EDC) (86.3 mg, 0.45 mmol) and 1-hydroxybenzotriazole (HOBt) (61.3 mg, 0.45 mmol) in DMF (3 ml) was added N, N-dsopropylethyamine, redistilled (DIPEA) (0.08 ml, 0.45 mmol). The mixture was stirred overnight, and then partitioned between ethyl acetate and water. The organic phase was washedwith brine, dried (MgSC>4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CHkMeOH = 6: 1) to give 3-[2-(4-iodo-phenoxy)acetyl-amino]-benzamide as a white solid (105.1 mg, 88.4% yield). 1H-NMR (DMSOKI6) 10.22 (IH, s, NH), 8.09 (IH, s, aromatic-H), 7.94(1H, s, NH2), 7.79 (IH, d, J =8.1 Hz, aromatic-H), 7.56 – 7.64 (3H, m, aromatic-H), 7.35 – 7.41 (2H, m, aromatic-H, NH2), 6.86 (2H, d, J= 8.7 Hz, aromatic-H), 4.71 (2H5 S3 CH2)., ..

Statistics shows that 2-(4-Iodophenoxy)acetic acid is playing an increasingly important role. we look forward to future research findings about 1878-94-0.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; WO2008/4798; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 672-57-1 name is 1-Chloro-2-iodo-4-(trifluoromethyl)benzene, 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. 672-57-1

General procedure: The corresponding iodobenzenederivative 14a or 14b (1.80 mmol) and 5-formyl furan-2-ylboronicacid 15 (2.34 mmol) were dissolvedin 10 mL DMF and 15 mL EtOH. The reaction mixture was stirred for 10 min underN2, then Pd(PPh3)2Cl2 (0.18 mmol)and a solution of Na2CO3 (2M, 10.8 mmol) were added to thereaction mixture, and the light-orange suspension was stirred under N2at room temperature. After 1 h the reaction went to completion (TLC) and wasquenched with 1M HCl, then EtOAc (10 mL) was added, and the mixture was stirreduntil the two layers became clear. The combined organic layers were washed withH2O and brine, dried over Na2SO4, filtered,and evaporated under reduced pressure. The crude product was purified by flashchromatography using PE/EtOAc as eluent to yield the desired product as a solid(yields: 8 (64%), 13 (87%)).

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

Reference:
Article; Botta, Lorenzo; Maccari, Giorgio; Calandro, Pierpaolo; Tiberi, Marika; Brai, Annalaura; Zamperini, Claudio; Canducci, Filippo; Chiariello, Mario; Marti-Centelles, Rosa; Falomir, Eva; Carda, Miguel; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2502 – 2505;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 6940-76-7, 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. 6940-76-7, name is 1-Chloro-3-iodopropane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.10 g, 0.50 mmol) in acetone (2 mL) was added 1 -chloro-3-iodo-propane (0.10 g, 0.50 mmol, 1 eq) and K2CO3 (0.084 g, 0.60 mmol, 1.2 eq). The mixture was heated at 50 0C for 3 h and then cooled to r.t. The mixture was filtered through Celite and the filtrate was concentrated in vacuo. Chromatography on silica gel by eluting with 5% EPO MthetaOH/CH2CI2 gave 0.095 g (69%) of 5-(3-chloro-propyl)-2,5-diaza- bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester as a yellowish oil. 1H NMR (300 MHz, CDCI3): delta 4.20 (m, 1 H), 3.58 (m, 2H), 3.46 (m, 2H), 3.12 (m, 1 H), 2.86 (m, 1 H), 2.62 (m, 3H), 1.82 (m, 3H), 1.66 (m, 1 H), 1.41 (s, 9H). By analogy to Preparative Example 8, substituted and/or unsubstituted 1-(3- chloro-propyl)-pyrrolidine and 1 -(3-chloro-propyl)-piperidine groups can be prepared with pyrrolidine and piperidine respectively.

The synthetic route of 1-Chloro-3-iodopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/44293; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, 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 112671-42-8, Recommanded Product: 4-Bromo-1-iodo-2-nitrobenzene

Under nitrogen conditions, 7H-diphenyl[c,g]carbazole (13.3 g, 49.92 mmol),4-bromo-1-iodo-2-nitrobenzene (32.74 g, 99.85 mmol),Potassium carbonate (13.8 g, 99.85 mmol), copper (6.35 g, 99.85 mmol),Stirring with ethylene glycol (350ml) at 100 CAfter stirring for about 1 hour, the reaction was completed, and after washing with deionized water,Recrystallization of acetone and methanol gave Intermediate 1-1 (15.9 g, 68%).

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

Reference:
Patent; Jilin Aolaide Optoelectric Materials Co., Ltd.; He Jinxin; Jiang Zhiyuan; Jiang Xiaochen; Suo Hongguang; Wang Jinzheng; Jin Furong; (14 pag.)CN109422756; (2019); 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. 6940-76-7, name is 1-Chloro-3-iodopropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H6ClI

a) Preparation of 5-Chloro-2-(3.4-dimethoxyphenyl)-2-isopropylpentanenitrile 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile (1.21 g, 5.52 mmol) was added to a suspension of sodium amide (0.59 g, 14.4 mmol) in toluene (12 ml). The mixture was then heated to reflux for 2 hours before the addition of 1-chloro-3-iodopropane (0.9 ml, 8.3 mmol). The mixture was cooled to room temperature over 80 minutes, and worked up by addition of water. The product was extracted with methyl-t-butyl ether (MTBE). After usual work-up, including drying the organic extract using MgSO4 and concentrating under reduced pressure the product was purified on column chromatography eluding with (ethyl acetate: light petroleum (b.p. 40 -60 C.) =1:2), to give 1.4g (82% yield) of the required product.

The synthetic route of 6940-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Darwin Discovery Limited; US5910601; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9, 624-75-9

Example 41 Benzyl {(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}(cyanomethyl)carbamate Potassium carbonate (15.7 mg, 113 mmol, 2.1 eq.), 18-crown-6 (30 mg, 113 mmol, 2.1 eq.) and iodoacetonitrile (19 mg, 113 mmol, 2.1 eq.) were added to a solution of benzyl {(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (30 mg, 54 mmol) in DMF (2 ml). The reaction mixture was stirred at RT for 12 h and then concentrated under reduced pressure. The residue was acidified with acetic acid and then purified by preparative HPLC (Kromasil C18 column, 5 mum, 50*20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (25 mg, 78% of theory). LC-MS (Method 5): Rt=1.40 min; MS (ESIpos): m/z (%)=434.0 (100), 550.9 (20), 595.0 (30) [M+H]+; MS (ESIneg): m/z (%)=593.8 (100) [M-H]-. 1H-NMR (400 MHz, DMSO-d6): delta=2.00 (s, 3H), 4.55 (d, 2H), 5.10 (d, 2H), 6.55 (s, 1H), 7.15-7.35 (m, 5H), 7.70-7.95 (m, 7H), 8.15 (br. s, 1H).

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, 2-Iodoacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2012/4203; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 63131-30-6, A common heterocyclic compound, 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, molecular formula is C11H11IO3, 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: To a solution of ethyl 3-oxo-3-(p-tolyl)propanoate (320 mg, 1.552 mmol) in dry DMF (3.1 mL) was added K2CO3 (236 mg, 1.707 mmol) followed by a solution of propargyl bromide in PhMe (9.2 M, 0.202 mL, 1.862 mmol). The reaction mixture was allowed to stir at ambient room temperature for 12 h. The reaction was transferred to a separatory funnel and diluted with deionized water (20 mL) and the aqueous layer was extracted with ethyl acetate (3 * 20 mL). The combined organic layers were sequentially washed with deionized water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate then concentrated in vacuo. The crude material was then purified by flash column chromotography (3% EtOAc/Hexanes) to provide 10 (313 mg, 82%) as a yellow oil.

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:
Article; Golonka, Alexander N.; Schindler, Corinna S.; Tetrahedron; vol. 73; 29; (2017); p. 4109 – 4114;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com