Category: 19718-49-1

Application 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 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

Electric Literature of 19718-49-1, 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.

To a stirred solution of 4-amino-3-iodo-benzoic acid methyl ester (11.1 g, 40.0 mmol) in pyridine (80 mL) was added acetyl chloride (3.30 g, 42.0 mmol) at 0 C. under nitrogen. Stirring continued at 0 C. for 30 minutes. The ice-bath was removed, and stirring continued at room temperature for 16 hours. Pyridine was evaporated under reduced pressure. The residue was taken in ethyl acetate (300 mL). The organic phase was washed with 2 N aqueous HCl (200 mL), water (200 mL), brine (200 mL), and then dried over anhydrous Na2SO4. Removal of solvent gave 4-acetylamino-3-iodo-benzoic acid methyl ester as a white solid. Yield: 12.71 g (99%)

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; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature 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 flask was charged with methyl 4-amino-3-iodobenzoate (7.50 g, 27.1 mmol, 1.00 equiv), DCM (50 mL), triethylamine (7.20 g, 71.3 mmol, 2.63 equiv) and trifluoroacetic anhydride (8.90 g, 42.4 mmol, 1.57 equiv), as described in Example 1, Step 1. The residue was chromatographed on a silica gel column to provide 8.00 g (79% yield) of methyl 3-iodo-4- (2,2,2-trifluoroacetamido)benzoate as a yellow solid.

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 4-amino-3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, 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 19718-49-1, HPLC of Formula: C8H8INO2

General procedure: A solution of 2-iodoaniline (333.6 mg, 1.52 mmol, 1.0 equiv) in DCM (5.0 mL) was added with Et3N (0.23 mL, 166.9 mg, 1.65 mmol, 1.1 equiv). The reaction solution was cooled at 0 C and acetyl chloride (0.28 mL, 308 mg, 3.92 mmol, 2.6 equiv) was added into the cooled solution. The resulting mixture was warmed to stir at room temperature overnight. Upon completion, thereaction was added with water and the separated aqueous phase was extracted with EtOAc (3xtimes). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30% EtOAc-hexane to yield 387.9 mg (98%) of the corresponding N-(2-iodophenyl)acetamide as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Chaisan, Nattawadee; Kaewsri, Wilailak; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak; Tetrahedron Letters; (2018); p. 675 – 680;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. Safety of Methyl 4-amino-3-iodobenzoate

A solution of 3.00 g (10.8 mmol) of methyl 4-amino-3-iodobenzoate and 1.30 g (54.1 mmol) of lithium hydroxide in 150 ml of a dioxane/water mixture (1:1) was stirred at room temperature for 6 h. The dioxane was distilled off in vacuo, and the remaining aqueous phase was adjusted to pH 5 with 1 M hydrochloric acid. The precipitate was filtered off with suction and washed with water. 2.80 g (98%) of the title compound were obtained as a solid. HPLC (Kromasil RP-18, 60*2.1 mm, eluent=A: H2O+5 mL HClO4/L; B: acetonitrile; gradient=0-4.5 min 98% A-90% B; 4.5-6.5 min 90% B; 0.75 mL/min; temp.: 30 C., UV detection at 21 nm): Rt=3.51 min 1H-NMR (300 MHz in D6-DMSO) delta=5.98 (s, 2H), 6.74 (d, 1H), 7.63 (m, 1H), 8.10 (s, 1H), 12.33 (s, broad, 1H) MS (ESI+): m/z=281 [M+NH4]+

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:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Hendrix, Martin; Boebeta, Frank-Gerhard; Erb, Christina; Krueger, Joachim; Luithle, Joachim; Methfessel, Christoph; Schreiber, Rudy; Wiese, Welf-Burkhard; US9139579; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19718-49-1, name is Methyl 4-amino-3-iodobenzoate, 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. name: Methyl 4-amino-3-iodobenzoate

To a stirred solution of Intermediate 14 (31.9 g, 107 mmol) in DMF (160 ml) was added methyl 4-amino-3-iodobenzoate (29.8 g 107 mmol), LiCl (4.5 g 107 mmol) and Na2CO3 (22.8 g 215 mmol). The resulting suspension was degassed, Pd(OAc)2 (0.96 g, 4.3 mmol) added, and degassing repeated. The reaction mixture was heated to HO0C for 50 minutes. The reaction mixture was then cooled to room temperature, filtered through celite and concentrated in vacuo. The resulting brown oil was separated between isopropyl acetate and water. The aqueous layer was back-extracted with isopropyl acetate (2 x 150 mL). The combined organic layers were dried (MgSO4), treated with decolourising charcoal (5% by weight of crude material) for 30 minutes at room temperature, and purified by column chromatography (SiO2, DCM) to give the title compound (9.0 g, 19%) as a pale cream solid. deltaeta (CDCl3) 8.50 (IH, br s), 8.05 (IH, s), 7.88 (IH, d), 7.32 (IH, d), 4.32 (IH, m), 3.99 (IH, t), 3.91 (3H, s), 3.65 (IH, d), 3.50-3.28 (3H, m), 3.05 (IH, dd), 1.48 (9H, s), 0.40 (9H, s). LCMS (ES+) 469.1 (M+Na).

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

Reference:
Patent; UCB PHARMA S.A.; WO2009/71888; (2009); 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. Product Details of 19718-49-1

Intermediate 1; Methyl 2-(trimethylsilyl)-3-f2-r(trimethylsilyl)oxy1ethyl)-1H-indole-5-carboxylate; Methyl 4-amino-3-iodobenzoate (27.7 g, 0.1 mol), LiCI (4.24 g, 0.1 mol), Cs2CO3 (81.5 g, 0.25 mol), tri(o-tolyl)phosphine (1.52 g, 5 mmol) was added to DMF (500 ml). The mixture was degassed with nitrogen and 4-trimethylsilyl-3-butyn-1-ol (26.67 ml, 0.16 mol) and palladium (II) acetate (1.12 g, 5 mmol) was added, The mixture was degassed with nitrogen and stirred at 100 0C for 3 hours. The reaction mixture was filtered on celite (5 cm) and evaporated. The crude extract was diluted with ethyl acetate, the organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified on SiO2 eluting with dichloromethane/ethyl acetate 95/5 to give a first fraction of the title compound (2.1 g) and a second fraction after evaporation and addition of heptane, precipitation and filtration : (Intermediate 1) (19.3 g, 66 %). LC/MS : m/z 292 (M+H)+, Rt: 2.96

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (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., COA of Formula: C8H8INO2

4-Amino-3-iodo-iV,./V-dimethylbenzamide < To a stirred solution of dimethylamine (9.0 mL, 135 mmol) in THF at O0C was added trimethylaluminium (50 mL, 2.0M solution in toluene, 100 mmol). The resulting solution was stirred at 00C for 10 minutes before addition of a solution of methyl 4- amino-3-iodobenzoate (19 g, 70 mmol) in THF (50 mL). The solution was heated to reflux for 1.5 h then allowed to cool to r.t before being poured onto ice (100 g). The resulting suspension was treated with aqueous 2M NaOH solution (100 mL) and partitioned with diisopropyl ether (2 x 100 mL). The combined organics were passed through a phase separator and concentrated to give the title compound (20 g, 96%) as a pale yellow oil which was used without further purification. 5H (CDCl3) 7.79 (IH, d, J 1.5 Hz), 7.29-7.26 (IH, m), 6.72 (IH, d, J8.2 Hz), 4.31 (2H, br. s), 3.07 (6H, s). LCMS (ES+) 261 (M+H)+.

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 19718-49-1.

Reference:
Patent; UCB PHARMA S.A.; WO2009/71888; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19718-49-1,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.

STEP D: 4-Amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide A 500 mL round bottom flask was charged with methyl 4-amino-3-iodobenzoate (10.0 g, 36.1 mmol), methanol (270 mL), water (30 mL), and lithium hydroxide (1.82 g, 43.3 mmol). The vessel was flushed with nitrogen, fit with a reflux condenser, and the mixture heated to a gentle reflux for 20 h. The resulting mixture was then cooled to room temperature, acidify with 2N hydrochloric acid, then concentrated in vacuo. A 500 mL round bottom flask was charged with the resulting solid (9.5 g, 36.7 mmol) and dichloromethane (180 mL) was added. Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (10.0 g, 39.5 mmol) and triethylamine (11.1 mL, 79.2 mmol) were added. 3,4-Dimethoxyaniline (11.1 g, 72.1 mmol) was then added and the resulting mixture was stirred at room temperature for 24 h. The resulting mixture was then diluted with ethyl acetate and washed with 1N NaOH. The organic layer was dried with MgSO4, filter, then concentrate in vacuo to yield 4-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide. 1H NMR (300 MHz, CDCl3) delta 8.23 (s, 1 H), 7.73 (d, J=8.5 Hz, 1H), 7.42 (s, 1H), 7.30 (d, J=8.6 Hz, 1H), 6.90 (d, J=8.8 Hz, 1H), 6.77 (d, J=8.5 Hz, 1H), 3.74 (s, 3H), and 3.72 (s, 3H).

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

Reference:
Patent; Lawson, Edward C.; Hlasta, Dennis J.; Ghosh, Shyamali; DesJarlais, Renee L.; Schubert, Carsten; US2011/152321; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com