Author: Jessica.F

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. 626-62-0, name is Iodocyclohexane, A new synthetic method of this compound is introduced below., COA of Formula: C6H11I

A mixture of zinc dust (16.34 g, 250 mmol, Aldrich, -325 mesh) and dry tetrahydrofuran (6 mL) under argon was treated with 1,2-dibromoethane (0.94 g, 5 mmol). The zinc suspension was then heated with a heat gun to ebullition, allowed to cool, and heated again. This process was repeated three times to make sure the zinc dust was activated. The activated zinc dust suspension was then treated with trimethylsilyl chloride (0.54 g, 5 mmol), and the suspension was stirred for 15 min at 25 C. The reaction mixture was then treated dropwise with a solution of cyclohexyl iodide (21 g, 100 mmol) in dry tetrahydrofuran (30 mL) over 15 min. During the addition, the temperature rose to 60 C. The reaction mixture was then stirred for 3 h at 40-45 C. The reaction mixture was then cooled to 25 C. and diluted with dry tetrahydrofuran (60 mL). The stirring was stopped to allow the excess zinc dust to settle down (3 h). In a separate reaction flask, a mixture of lithium chloride (8.48 g, 200 mmol, predried at 130 C. under high vacuum for 3 h) and copper cyanide (8.95 g, 100 mmol) in dry tetrahydrofuran (110 mL) was stirred for 10 min at 25 C. to obtain a clear solution. The reaction mixture was cooled to -70 C. and then slowly treated with the freshly prepared zinc solution using a syringe. After the addition, the reaction mixture was allowed to warm to 0 C. where it was stirred for 5 min. The reaction mixture was again cooled back to -70 C. and then slowly treated with methyl propiolate (7.56 g, 90 mmol). The resulting reaction mixture was stirred for 15 h at -70 C. to -50 C. and then slowly treated with a solution of iodine (34.26 g, 135 mmol) in dry tetrahydrofuran (30 mL), with the temperature kept at -70 C. to -60 C. After addition of the iodine solution, the cooling bath was removed, and the reaction mixture was allowed to warm to 25 C. where it was stirred for 2 h. The reaction mixture was then poured into a solution consisting of a saturated aqueous ammonium chloride solution (400 mL) and ammonium hydroxide (100 mL), and the organic compound was extracted into ethyl acetate (3250 mL). The combined organic extracts were successively washed with a saturated aqueous sodium thiosulfate solution (1500 mL) and a saturated aqueous sodium chloride solution (1500 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 9/1 hexanes/diethyl ether) afforded (E)-3-cyclohexyl-2-iodo-acrylic acid methyl ester (26.3 g, 99%) as a light pink oil: EI-IIRMS m/e calcd for C10H15IO2 (M+) 294.0117, found 294.0114.

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; Hoffmann-La Roche Inc.; US6353111; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 98-61-3, 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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To the ammonium hydroxide (5.0 mL) was added 4-iodo-benzenesulfonyl chloride (454.0 mg, 1.5 mmol). The resulting mixture was stirred at room temperature for 2 h and extracted with DCM (2 × 20.0 mL). The combined organic phase was dried over anhydrous Na2SO4, and concentrated to give 39 as a white solid (392.0 mg). 1H NMR (400 MHz, DMSO-d6): delta 7.98-7.96 (d, J = 8.6 Hz, 2H), 7.60-7.58 (d, J = 8.6 Hz, 2H), 7.45 (s, 2H).

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, 4-Iodobenzenesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Kai; Rao, Wei; Parikh, Hardik; Li, Qianbin; Guo, Tai L.; Grant, Steven; Kellogg, Glen E.; Zhang, Shijun; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 125 – 137;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 672293-33-3, name is Methyl 4-amino-5-iodo-2-methylbenzoate, 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. COA of Formula: C9H10INO2

[0069] Methyl (2-(l-oxopeutyl)-3-(2-phenylethyl)-6-methyl)indole-5-carboxyIate (7); Amixture of 4 (250 mg), l-triethylsilyl-4-phenylbutyne (5, 320 mg), palladium acetate (30 mg), sodium carbonate (450 mg), and degassed DMF (2 mL) was stirred at 100C under argon atmosphere for 5 hours. The reaction mixture was filtered through fluorisil, eluted with 20% ethyl acetate/hexanes and evaporated to afford indole 6 as an amorphous. To a mixture of 6, dichloromethane (3 mL) and valeryl chloride (0.52 mL), zinc chloride (1M in diethyl ether solution, 0.77 mL) was added slowly at 4C, and stirred at 4C for 3 hours. The reaction mixture was treated with methanol (3 mL), diluted with ethyl acetate (30 mL), washed with water twice (10 mL each), aqueous sodium carbonate (10 mL) followed by brine (10 mL), dried (Na2S04), and evaporated. The crude residue was washed with hexanes to give 7 (165 mg) as a brown solid. Mp 145-147C; ]H NMR (CDC13, 400 MHz) 8 8.87 (s, 1H), 8.32 (s, 1H), 7.30-7.20 (m, 3H), 7.19 (s, 1H), 7.14 (d, J= 7.6 Hz, 2H), 3.93 (s, 3H), 3.39 (t, J= 8.4 Hz, 2H), 3.01 (t, J= 7.2 Hz, 2H), 2.74 (t, J= 7.6 Hz, 2H), 2.71 (s, 3H), 1.68 (quintet, J= 7.6 Hz, 2H), 1.68 (dt, J= 7.6 Hz, 15.2 Hz, 2H), 0.95 (t, J= 7.2 Hz, 3H).

The synthetic route of Methyl 4-amino-5-iodo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/7542; (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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,2-Dichloro-4-iodobenzene

[0268] To a solution of 1,2-dichloro-4-iodobenzene (1.0 g, 3.68 mmol) in ether (10 mL) at 0 C. was added iPrMgCl (2.2 mL, 2M in Et2O) dropwise and the resulting solution stirred at 0 C. for 30 minutes and room temperature 1 hour. The reaction mixture was recooled to 0 C. and cyclopropylacetonitrile (0.34 mL, 1.0 eq.) was added. The reaction mixture was stirred at 0 C., room temperature 1 hour, then quenched by the addition of 1N HCl. The resulting solution was stirred at room temperature 2 hours and extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography using a 100% hexanes to 10% EtOAc in hexanes solution gradient as eluent (0.10 g, 21% yield). LCMS: MH+=227.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20555-91-3.

Reference:
Patent; Schering Corporation; US2003/232837; (2003); 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. 6293-83-0, name is 2-Iodo-4-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6293-83-0

To the solution of 2-iodo-4-nitroaniline (3.0 g, 11 mmol) in DMF (60 mL) and Et3N (60 mL) was added 2-ethynylpyridine (3.0 g, 45 mmol), Pd(PPh3)2Cl2 (600 mg) and CuI (200 mg) under N2. The reaction mixture was stirred at 60 C. for 12 h. The mixture was diluted with water and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 4-nitro-2-(pyridin-2-ylethynyl)aniline (1.5 g, 60%). 1H NMR (300 MHz, CDCl3) delta 8.60 (s, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.98 (d, J=1.8, 6.9 Hz, 1H), 7.87-7.80 (m, 2H), 7.42-7.39 (m, 1H), 7.05 (brs, 2H), 6.80 (d, J=6.9 Hz, 1H).

According to the analysis of related databases, 6293-83-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; US2007/244159; (2007); 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. 20691-72-9, name is 4-Iodo-2-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodo-2-nitroaniline

4-iodo-2-nitroaniline (2.64 g, 10.0 mmol)Was dissolved in 80% ethanol (60 mL)Concentrated hydrochloric acid (2.5 mL) was added.Iron powder (2.23 g, 40.0 mmol) was added,And the mixture was heated under reflux for 6 hours under stirring.After returning to room temperature,The precipitate was filtered,The solvent was distilled off under reduced pressure.After extraction with ethyl acetate (100 mL × 2) and saturated aqueous sodium hydrogen carbonate solution,The organic layer was washed with saturated brine.After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/1 (volume ratio)) as an elution solvent,Compound 9 was obtained in a yield of 1.98 g (89.1%).

According to the analysis of related databases, 20691-72-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyoto University; Nihon Medi-Physics Co.,Ltd.; Saji, Hideo; Ono, Masahiro; Inohara, Tadashi; Seki, Ikuya; (24 pag.)JP2016/79108; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Phosphorus oxychloride (1.47 g, 9.6 mmol, 0.9 mL) was added dropwise at -10 C to a stirred pyridine (40 mL) solution of N-Boc-L-proline 7 (1.74 g, 8.08 mmol) and arylamine 6 (2.24 g, 8.08 mmol) under argon atmosphere. The reaction mixture was stirred for 30 min (-10-5 C), then poured into water (200 mL) containing ice, and extracted with EtOAc. The aqueous layer was additionally extracted with EtOAc. The extract was washed with water, saturated NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using CHCl3 as the eluent. The isolated product with Rf 0.56 (EtOAc/LP, 1 : 2) was crystallized from petroleum ether to give amide 8 (2.8 g, 74%) as light brown crystals, m.p. 92-95 C, [alpha]23D -103.96 (c = 1.0, CHCl3). 1H NMR (CDCl3), delta: 1.35 and 1.49 (both br.s, integral ratio of 5/4, 9 H, Me3C); 1.74-2.42 (m, 4 H, HC(4), HC(5)); 3.39-3.80 (m, 2 H, HC(3)); 3.91 (s, 3 H, MeO); 4.27 and 4.41 (both m, integral ratio of 5/4, 1 H, HC(1)); 7.81 (br.d, 1 H, HC(3), J = 8.2 Hz); 8.34 (br.s, 1 H, HC(4)); 8.57 (br.d, 1 H, HC(6), J = 8.2 Hz); 11.43 (m, 1 H, HN) (mixture of rotamers, see Ref. 21).

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 6940-76-7, 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. 6940-76-7 name is 1-Chloro-3-iodopropane, 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.

To a solution of TMEDA (4.36 mL, 28.9 mmol) in THF (30 mL) at -20 C was added n- butyllithium (12.03 mL, 28.9 mmol, 2.4 M solution in hexanes) over ten minutes. The mixture was stirred at 10 C for 30 minutes, then cooled to -78 C, and a solution of tert- butyl (6-chloropyridin-2-yl)carbamate (3 g, 13.12 mmol) in THF (15 mL) was added over a period of 5 minutes. After 40 minutes, copper(I) iodide (2.499 g, 13.12 mmol) was added, and the mixture was stirred at -10 C for 1 hour. l-Chloro-3-iodopropane (2.113 mL, 19.68 mmol) was added over a period of 1 minute, and the mixture was allowed to reach room temperature. After 2.5 hours the mixture was added to saturated aqueous sodium hydrogencarbonate and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was stirred in dichlorom ethane (30 mL), filtered through a glass- sintered funnel and concentrated to half volume and then applied onto a flash column (120 g silica), eluting with 2-20% ethyl acetate in heptane. The eluent coming off the column was passed through a column of potassium carbonate. This gave the desired product tert-butyl 7- chloro-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate (2.637 g). Yield 74% NMR (400 MHz, Chlorofomwf) d 7.32 (d, J = 7.9 Hz, 1H), 6.94 (d, J = 7.8 Hz, 1H), 3.81 – 3.69 (m, 2H), 2.73 (t, J= 6.6 Hz, 2H), 1.93 (p, J= 6.5 Hz, 2H), 1.54 (s, 9H).

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

Reference:
Patent; MORPHIC THERAPEUTIC, INC.; HARRISON, Bryce, A.; DOWLING, James, E.; GERASYUTO, Aleksey, I.; BURSAVICH, Matthew, G.; TROAST, Dawn, M.; LIPPA, Blaise, S.; ROGERS, Bruce, N.; ZHONG, Cheng; QIAO, Qi; LIN, Fu-Yang; SOSA, Brian; BORTOLATO, Andrea; SVENSSON, Mats, A.; HICKEY, Eugene; KONZE, Kyle, D.; DAY, Tyler; KIM, Byungchan; (124 pag.)WO2020/47208; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7,Some common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, 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 solution of methyl 3-iodobenzoate (4.5 g, 17.2 mmol) in DMSO (30 mL) was added 3-azetidin-3-ol hydrogen chloride salt (1.3 g, 11.8 mmol), Cs2CO3 (9.5 g, 29.2 mmol), CuI (446 mg, 2.3 mmol) and L-proline (540 mg, 4.7 mmol) and then the mixture was heated at 90 C. for 18 h under argon atmosphere. The solution was diluted with EA and water and the organic layer was washed with brine three times, concentrated under reduced pressure and purified by CC (PE/EA=2:1) to give compound 3a (1.6 g, 66%) as a yellow solid

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

Reference:
Patent; PHENEX PHARMACEUTICALS AG; Kinzel, Olaf; Steeneck, Christoph; Kremoser, Claus; US2014/221659; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, molecular formula is C7H4FIO2, 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. Formula: C7H4FIO2

(2-Fluoro-6-iodophenyl)methanol.; To a stirred solution of 2-fluoro-6-iodobenzoic acid (10 mmol) in THF (6.5 mL) and trimethylborate (3.25 mL) was added borane dimethylsulfide (12 mmol) slowly, maintaining the internal temperature at 20-25 C. Stirring was continued for an additional 16 h at room temperature and then methanol (1.44 mL) was added cautiously. The resulted solution was evaporated in vacuo to offer 2.5 g of the title compound as a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 111771-08-5, its application will become more common.

Reference:
Patent; PHARMACOPEIA, INC.; US2008/85898; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com