Category: 19718-49-1

Synthetic Route of 19718-49-1, 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) 1H-Indole-2,5-dicarboxylic acid 5-methyl ester A solution of 25 g 4-Amino-3-Iodo-benzoic acid methyl ester, 19 ml 2-Oxo-propionic acid, 30.4 g 1,4-Diaza-bicyclo[2.2.2]octane and 1 g Pd(OAc)2 in 200 ml DMF was heated under argon to 100 C. After 5 h the reaction mixture was concentrated under reduced pressure and the residue was partitioned between 300 ml ethyl acetate and 200 ml 1 M hydrochloric acid. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to yield a yellow solid (6.4 g). From the aqueous layer additional product slowly precipitated as a white solid (7.9 g) which was collected by filtration. Both fractions were combined, dried in vacuo and used in the next reaction without further purification. Yield: 14.3 g. MS (ES+): m/e=220.

The synthetic route of Methyl 4-amino-3-iodobenzoate has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, molecular formula is C8H8INO2, 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 Methyl 4-amino-3-iodobenzoate

General procedure: To a solution of vinyl bromide a-c (6.7 mmol) in dioxane (30 mL) at 25 C under argon were successively added Et3N (3.70 mL, 26.9 mmol), Pd (PPh3)4 (779 mg, 0.670 mmol), and pinacolborane (2.90 mL, 20.2 mmol) dropwise. The solution was heated to 80 C for 1 h. After cooling, water (5 mL) was added dropwise followed by methyl 4-amino-3-iodobenzoate (1.5 g, 5.4 mmol) dissolved in dioxane (15 mL) and Ba(OH)2¡¤8H2O (6.40 g, 20.2 mmol). The solution was heated to 90 C for 8 h. After cooling, the mixture was filtered through Celite, brine was added (40 mL), and the solution was extracted with ethyl acetate (3 ¡Á 50 mL). After drying over magnesium sulfate and evaporation of the solvents under vacuum, the residue was purified by flash chromatography to obtain the benzoates.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19718-49-1, its application will become more common.

Reference:
Article; Li, Yanwu; Silamkoti, Arundutt; Kolavi, Gundurao; Mou, Liyuan; Gulati, Shelly; Air, Gillian M.; Brouillette, Wayne J.; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4582 – 4589;,
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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 4-amino-3-iodobenzoate

A suspension of methyl 4-amino-3-iodobenzoate (500 mg, 1.81 mmol), 1 -methyl -4-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (563 mg, 2.71 mmol), Pd(dppf)Cl2 (132 mg, 0.18 mmol) and Cs2C03 (1177 mg, 3.61 mmol) in Dioxane/H20 (10 mL/2 mL) was stirred at 90C for 8h under Nitrogen. The mixture was then diluted with H20 (30 mL) and extracted with DCM (30 mL*2). The combined organic phases were concentrated in vacuo and the residue was purified by flash chromatography on silica gel (Petroleum Ether/Ethyl Acetate = 1/1) to afford methyl 4- amino-3-(l-methyl-lH-pyrazol-4-yl)benzoate (417 mg, 100%) as a brown solid. MS Calcd.: 231, MS Found: 232 ([M+H]+).

According to the analysis of related databases, 19718-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 19718-49-1, A common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, molecular formula is C8H8INO2, 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.

A solution of methyl 4-amino-3-iodobenzoate (1.0 g, 3.61 mmol) and triethylamine (1.003 mL, 7.22 mmol) in dichloromethane (20 mL) was added dropwise to a cooled (0 0C) solution of trifiuoroacetic anhydride (1.275 mL, 9.02 mmol) in dichloromethane (5 mL). The cooling was removed, the mixture was stirred at room temperature for 3 hours, poured into ice-water and extracted with dichloromethane. The organic phase was dried over sodium sulfate and the solvent was evaporated. Purification by column chromatography, using heptane/ethyl acetate (4:1) as the eluent, gave 1.23 g (91% yield) of the title compound. 1H NMR (500 MHz, CD3OD) delta ppm 8.54 (d, 1 H) 8.07 (dd, 1 H) 7.57 (d, 1 H) 3.93 (s, 3 H); MS (ESI) m/z 372 [M-I]”.

The synthetic route of 19718-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2009/64251; (2009); 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 4-amino-3-iodobenzoate

A combined suspension of methyl 4-amino-3-iodobenzoate (3.0 g, 10.83 mmol), copper (_) iodide (41 mg, 0.22 mmol), bis(triphenylphosphine)palladium(II) dichloride (152 mg, 0.22 mmol), and 1-ethynyl-3-methoxybenzene (1.69 mL, 12.99 mmol) were stirred in toluene and TEA (1/1, 90 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain the compound 47 as a white solid (3.00 g, 98% yield): 1H NMR (400 MHz, CDCl3) _ 8.07 (d, J = 2.1 Hz, 1H), 7.78 (dd, J = 8.2, 2.0 Hz, 1H), 7.21 (t, J = 7.9 Hz, 1H), 7.08 (dt, J = 7.7, 1.2 Hz, 2H), 7.03- 7.02 (m, 2H), 6.87- 6.86 (m, 1H), 6.66 (d, J = 8.6 Hz, 1H), 4.90 (s, 2H), 3.82 (s, 3H), 3.74 (s, 3H); 13C NMR (100 MHz, CDCl3) _ 166.5, 159.2, 151.7, 134.3, 131.3, 129.4, 123.8, 123.7, 118.8, 116.2, 114.8, 113.2, 106.7, 94.9, 84.6, 55.1, 51.6.

According to the analysis of related databases, 19718-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, 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. Application In Synthesis of Methyl 4-amino-3-iodobenzoate

(i) 1H-Indole-2,5-dicarboxylic acid 5-methyl ester A solution of 25 g 4-Amino-3-iodo-benzoic acid methyl ester, 19 ml 2-Oxo-propionic acid, 30.4 g 1,4-Diaza-bicyclo[2.2.2]octane and 1 g Pd(OAc)2 was heated under argon to 100 C. After 5 h the reaction mixture was concentrated under reduced pressure and the residue was partitioned between 300 ml ethyl acetate and 200 ml 1 M hydrochloric acid. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to yield a yellow solid (6.4 g). From the aqueous layer additional product slowly precipitated as a white solid (7.9 g) which was collected by filtration. Both fractions were combined, dried in vacuo and used in the next reaction without further purification. Yield: 14.3 g MS (ES+): m/e=220.

The synthetic route of Methyl 4-amino-3-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nazare, Marc; Essrich, Melanie; Will, David William; Matter, Hans; Ritter, Kurt; Wehner, Volkmar; US2003/199689; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 19718-49-1 as follows. Safety of Methyl 4-amino-3-iodobenzoate

A combined suspension of methyl 4-amino-3-iodobenzoate (2.74 g, 9.90 mmol), copper (_) iodide (38 mg, 1.98 mmol), bis(triphenylphosphine)palladium(II) dichloride (139 mg, 1.98 mmol), and 5-ethynylbenzo[d][1,3]dioxole (1.74 g, 11.89 mmol) were stirred in toluene and TEA (1/1, 82 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain the compound 48 as a white solid (2.92 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 8.04 (d, J = 2.0 Hz, 1H), 7.78 (dd, J = 8.6 ,2.0 Hz, 1H), 7.03 (dd, J = 8.0, 1.6 Hz, 1H), 6.94 (d, J = 1.6 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 6.67 (d, J = 8.6 Hz, 1H), 5.97 (s, 2H), 4.74 (bs, 2H), 3.85 (s, 3H); 13C NMR (100 MHz, CDCl3) _ 166.7, 151.5, 148.1, 147.5, 134.3, 131.3, 126.2, 119.3, 116.1, 113.3, 111.4, 108.6, 107.2, 101.5, 95.1, 83.2, 51.8.

According to the analysis of related databases, 19718-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com