Iodides-buliding-blocks

Some common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-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. Application In Synthesis of 2-Fluoro-5-iodobenzoic acid

A stirred suspension of 2-fluoro-5-iodobenzoic acid (99.7 g) in DCM (1 L) at 200C was treated with oxalyl chloride (49.8 mL) and DMF (0.3 mL). After 3 h further DMF (0.1 mL) was added. After a further 2 h the clear solution was evaporated and re-evaporated from toluene (3 x 200 mL). The acid chloride was re-dissolved in toluene (1.5 L) and treated with triethylamine (79.2 mL) and ethyl 3-(dimethylamino)acrylate (65.3 g). After stirring for 2.5 h at 900C the mixture was filtered and evaporated. The residue was redissolved in EtOAc, washed with saturated sodium hydrogen carbonate solution (2x), water, saturated brine, dried (MgSO4) and treated with decolourising charcoal for 0.5 h. The mixture was filtered, evaporated, redissolved in diethyl ether and allowed to crystallise. The solid was filtered off, washed with diethyl ether and dried to give the title compound (91.2 g). On concentration and seeding a second crop was obtained (9.0 g); ESMS m/z 391.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 124700-41-0, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/54295; (2007); 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.

Intermediate 11Z)-Ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2-Fluoro-5-iodobenzoic acid (5.20 g, 19.55 mmol, Aldrich) was suspended in thionyl chloride (1.427 mL, 19.55 mmol, Aldrich) and heated to reflux for 30 min. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to a tan solid. The solid was dissolved in toluene (30 mL) and concentrated under reduced pressure again. To a solution of the resulting solid (5.20 g, 19.55 mmol) in toluene (30 mL) was added triethylamine (2.72 mL, 19.55 mmol, Acros) and (Z)-ethyl 3-(dimethylamino)acrylate (3.64 mL, 25.41 mmol, Acros) and the reaction mixture was heated to 90 C. for 1 h. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by Isco column (0%-100% ethyl acetate/dichloromethane) afforded the desired compound as a yellow solid (6.51 g).MS (ES) (M+H)+: 392 for C14H15FINO3 1H NMR: 0.88 (t, 3H), 2.78 (s, 3H), 3.33 (s, 3H), 3.85 (q, 2H), 7.03 (dd, 1H), 7.65 (dd, 1H), 7.77 (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, 2-Fluoro-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2010/317624; (2010); 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. 624-76-0, name is 2-Iodoethanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 624-76-0

Step 2 tert-Butyl-(2-iodo-ethoxy)-dimethyl-silane To 2-iodoethanol (20 gm, 116 mmol) suspended in methylene chloride (500 mL) was added dimethylaminopyridine (100 mg) followed by diisopropylethylamine (30 mL, 174 mmol) and tert-butyldimethylsilyl chloride (19 gm, 128 mmol). The reaction was stirred overnight and the solvent was removed in vacuo and the residue was passed through a short column of silica gel and eluted with 95:5 methylene chloride: methanol. The desired fractions were combined and the solvent was removed in vacuo to give the desired product. 1 H NMR (400 MHz, CDCl3) delta 3.84 (dd, 2H); 3.20 (dd, 2H); 0.9 (m, 9H); 0.1 (m, 6H).

According to the analysis of related databases, 624-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US5939439; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 216393-67-8, A common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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 20 mL dehydrated deoxygenated Schlenk tube, acetophenone p-toluenesulfonylhydrazone(0.30 mmol, 86.4 mg), 4-chloro-2-fluoro-6-iodoaniline (0.2 mmol, 54.2 mg), bistriphenylphosphine(0.02 mmol, 14.0 mg), sodium tert-butoxide (1.2 mmol, 115.2 mg) 3.0 mL diethylene glycol dimethyl ether (diglyme), and finally 0.1 MPa of CO2 was injected into the reaction tube. The sealed reaction tube was heated and stirred in an oil bath at 140 C for about 24 hours Rear. The reaction solution was acidified with 1.5 mL of a 1 M hydrochloric acid solution and extracted with ethyl acetate (4 mL x 5) The organic phases were combined and finally the product was purified by column chromatography and then dried to give 29.5 mg of a white solid powder as a solid54%.

The synthetic route of 216393-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changzhou University; Sun, Song; Cheng, Jiang; Hu, Weiming; Gu, Ning; Wang, Bingbing; (12 pag.)CN106432074; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 90347-66-3, These common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-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.

Step 2: To a round-bottom flask containing 3-iodo-4-methyl-benzoic acid methyl ester (1.38 g, 5.00 mmol), 4-cyanophenylboronic acid (1.10 g, 7.48 mmol), palladium acetate (168 mg, 0.748 mmol), 2-(dicyclohexylphosphino)biphenyl (0.526 g, 1.50 mmol) and potassium fluoride (0.870 g, 15.0 mmol) is added anhydrous 1,4-dioxane (15 ml). The flask is purged with argon and sealed. The mixture is stirred at 130 C. for 18 hours, cooled to ambient temperature and then water (20 ml) and ethyl acetate (20 ml) are added. Solid is removed under vacuum filtration. The filtrate is extracted with EtOAc (20 ml*2). The organic layers are combined, washed with aqueous HCl (5%, 20 ml) and saturated NaHCO3 (20 ml). It is dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient) to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester 2; LC-MS m/z: 252.1 (M+1).

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; US2010/197659; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 69113-59-3, A common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, molecular formula is C7H4IN, 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.

Add trimethylsilylacetylene (3. 4 mL, 24. 0 mmol) to a mixture of bis (triphenylphosphine) palladium (II) dichloride (766 mg, 1. 1 mmol), copper (I) iodide (418 mg, 2. 2 mmol) and 3-iodobenzonitrile (5 g, 21. 8 mmol) in triethylamine (20 mL). Upon addition of the trimethylsilylacetylene an exothermic reaction occurs and after about 4 min the reaction mixture solidifies. Cool the reaction mixture for about 15 min, dilute with ethyl acetate (100 mL), filter through fluted filter paper using ethyl acetate and concentrate. Dissolve the residue in ethyl acetate (200 mL) and wash sequentially with an aqueous solution of 0. 1 N hydrochloric acid and a saturated aqueous solution of sodium chloride. Dry (sodium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 0 : 100 to 5 : 95 ethyl acetate : hexanes, to give the title compound as a tan solid (3. 6 g, 83%). 1H NMR (400 MHz, CDC13) 8 0. 29 (s, 9H), 7. 45 (t, J = 8. 0 Hz, 1H), 7. 60-7. 63 (m, 1H), 7. 68-7. 71 (m, 1H), 7. 77-7. 78 (m, 1H). LC-MS (ES) : m/z = 200. 0 [M+H+.

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; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 oC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 105-107 C; 1H NMR (400 MHz, CDCl3) delta 8.09 (s, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 3.73 (s, 2H), 3.30(s, 2H), 2.40 (s, 3H), 1.07 (s, 6H); 13C NMR (100 MHz, CDCl3) delta 161.6, 136.5, 134.6, 131.2, 129.7, 124.1, 122.0, 57.0, 52.5, 27.9, 24.2, 20.8 ppm. Anal. Calcd. for C14H16N2OS: C 64.58, H 6.19, N 10.76; found: C 64.25, H 6.27, N 10.49; EI-MS: m/z = 260 (M+)

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
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. 116632-39-4, name is 5-Bromo-2-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-2-iodotoluene

In dioxane (5 mL) solution of tert-butyl 5-hydroxy-4-methyl-2,3-dihydro-1H-indole-1-carboxylate (250 mg) and 5-bromo-2-iodo toluene (212 muL), copper iodide (I) (38.1 mg), N,N-dimethyl glycine (41.2 mg), cesium carbonate (651 mg) was added and stirred for 24 hours at 100 C. The reaction mixture into a saturated ammonium chloride solution (6 mL), saturated aqueous sodium bicarbonate (3 mL), and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After washing the resulting residue with hexane, collected by filtration, and dried to give the title compound (57.5 mg) as a white solid.

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 116632-39-4.

Reference:
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; GOTO, TAIJI; SASAKI, JUNKO; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (97 pag.)JP2016/108257; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 144550-76-5, 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. 144550-76-5, name is Methyl 2-amino-4-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

C. 4-Iodo-2-(Quinoxaline-5-sulfonylamino)benzoic acid methyl ester. A solution of methyl 2-amino-4-iodobenzoate (1.2 g, 4.4 mmol), quinoxaline-5-sulfonyl chloride (1.2 g, 5.3 mmol), pyridine (1.7 mL, 22 mmol) and DCM (25 mL) was maintained at 23 C. for 24 h. The reaction mixture was diluted with DCM (200 mL) and washed with satd. aq. NaHCO3, then dried and concentrated to a tan solid. This residue was chromatographed (0 to 100% EtOAc/CH2Cl2) to afford the sulfonamide as a light yellow solid (1.6 g, 77%). MS (ESI): calculated for C16H12IN3O4S, 469.0; m/z found, 470 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 11.10 (s, 1H), 9.07 (d, J=1.8 Hz, 1H), 9.01 (d, J=1.8 Hz, 1H), 8.60 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (dd, J=8.5, 1.3 Hz, 1H), 8.04 (dd, J=7.5, 1.0 Hz, 1H), 7.99 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.37 (dd, J=8.3, 1.6 Hz, 1H), 3.88 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-55-7,Some common heterocyclic compound, 103440-55-7, name is Methyl 2-iodo-6-methylbenzoate, molecular formula is C9H9IO2, 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.

Methyl 2-iodo-6-methylbenzoate (158) (2.00 g, 7.245 mmol) and NBS (1.418 g, 7.969 mmol) were stirred in chlorobenzene (50 mL) and benzoyl peroxide (75% w/w, 0.234 g, 0.724 mmol) was added. The reaction was stirred at 90 C for 18 hours, cooled to room temperature, filtered and the precipitate was washed with cyclohexane (4×10 mL). The combined filtrates were evaporated, and the resulting brown oil was diluted with THF (50 mL). Aqueous ammonia solution (20 mL) was added, and the mixture was stirred vigorously for 1 hours. The mixture was diluted with water (20 mL) and the THF was removed in vacuo. DCM (150 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (2x 00 mL), the combined organics were washed with brine (100 mL), dried (MgS04) and filtered. Silica gel was added and the volatiles were removed in vacuo to give the crude material absorbed onto silica gel. The material was purified by silica gel chromatography (Biotage Isolera, 40 g Si cartridge, 0-100% EtOAc in petroleum benzine 40-60 “C, then 0-20% methanol in EtOAc) to give the title compound (159) (0.757 g, 40% yield) as a beige solid; 1H NMR (400 MHz, CDCI3) delta 7.93 (dd, J = 7.8, 0.7 Hz, 1 H), 7.46 (dd, J = 7.5, 0.8 Hz, 1 H), 7.26 – 7.21 (m, 1 H), 7.10 (br s, 1 H), 4.37 (d, J = 0.6 Hz, 2H). LCMS Method C: rt 5.06 min; m/z 260.0 IM+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-iodo-6-methylbenzoate, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com