Category: 19718-49-1

Electric Literature 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 mixture of methyl 4-amino-3-iodobenzoate (5. OG, 18.0 mmol), di-tert-butyl dicarbonate (4.7g, 21.7 mmol), triethylamine (7.6 mL, 54.2 mmol), 4- (dimethylamino) pyridine (22mg, 0.18 mmol), and dichloromethane (150 mL) was heated overnight at 40 C, cooled to room temperature, concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MGS04), filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the 3.4g (50%) of the desired product. MS (ESI) m/e 395 (M+NH4) + ; IH NMR (300 MHz, DMSO-D6) 8 8.51 (s, 1H), 8.33 (d, J=2.0 Hz, 1H), 7.92 (dd, J=2.0, 8.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 3.84 (s, 3H), 1.48 (s, 9H).

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; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products 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 combined suspension of methyl 4-amino-3-iodobenzoate (2.50 g, 9.02 mmol), copper (_) iodide (35 mg, 0.18 mmol), bis(triphenylphosphine)palladium(II) dichloride (127 mg, 0.18 mmol), and 1-ethynyl-4-methylbenzene (1.37 mL, 10.83 mmol) were stirred in toluene and TEA (1/1, 76 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 (5/1, v/v) to obtain the compound 44 as a white solid (2.39 g, quant. yield): 1H NMR (400 MHz, DMSO-d6) _ 7.81 (d, J = 2.0 Hz, 1H), 7.65 (dd, J = 8.7, 2.1 Hz, 1H), 7.56- 53 (m, 2H), 7.24- 7.21 (m, 2H), 6.76 (d, J = 8.7 Hz, 1H), 6.36 (s, 2H), 3.75 (s, 3H), 2.33 (s, 3H); 13C NMR (100 MHz, DMSO-d6) _ 165.7, 153.4, 138.2, 133.8, 131.4, 131.0, 129.2, 119.6, 116.2, 113.2, 105.1, 94.4, 84.9, 51.5, 21.1.

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

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

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

j00292J A round-bottom 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). The resulting solution was stirred overnight at room temperature and washed with water (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, 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 yell ow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; WIENER, John J. M.; CISAR, Justin S.; DUNCAN, Katharine K.; (324 pag.)WO2018/217809; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 19718-49-1, 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.

Intermediate 4; Methyl 3-r2-alpha2-r(1.1-dimethylethyl)oxy1-2-oxoethyl)oxy)ethv?-2-(trimethylsilyl)-1H- indole-5-carboxylate FOPI/U1435/60/1; Pd(OAc)2 (106 mg, 0.47 mmol) was added to a solution of methyl 4-amino-3-iodobenzoate (2.58 g, 9.3 mmol), 1 ,1-dimethylethyl {[4-(trimethylsilyl)-3-butyn-1-yl]oxy}acetate (Intermediate 3) (3.8 g, 14.8 mmol), LiCI (394 mg, 9.3 mmol), Cs2CO3 (7.58 g, 23.25 mmol) and tri-o-tolylphosphine (143 mg, 0.47 mmol) in anhydrous DMF. The reaction mixture was stirred at 100 0C for 3 hours. The reaction mixture was filtered and rinse with dichloromethane. The filtrate was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified on SiO2 eluting with dichloromethane to give the title compound (1.65 g, 44%). LC/MS : m/z 406 (M+H)+, Rt: 3.96.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 19718-49-1, 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.

INTERMEDIATE 42 Methyl 3-{[(3^-4-(tert-butoxycarbonvnmorpholin-3-yl1methvU-2-ftrimethylsilyl’)-l//- intlupsilonle-5-earbupsilonxyldleTo a stirred solution of Intermediate 41 (31.9 g, 107.4 mmol) in DMF (160 mL) was added methyl 4-amino-3-iodobenzoate (29.8 g, 107.4 mmol), lithium chloride (4.5 g, 107.4 mmol) and sodium carbonate (22.8 g, 214.8 mmol). The resulting suspension was degassed before addition of palladium acetate (0.96 g, 4.3 mmol). The reaction mixture was heated to 11O0C for 50 minutes. It was cooled to r.t, filtered through celite, and concentrated in vacuo. The resulting brown oil was partitioned between isopropyl acetate and water (150 mL each). The aqueous fraction was extracted with isopropyl acetate (2 x 15OmL). The combined organic fractions were dried (MgSO4), treated with decolourising charcoal (5% by weight of crude material) for 30 minutes at room temperature, concentrated in vacuo and then purified by column chromatography (SiO2, DCM) to give the title compound (9g, 19%) as a pale cream solid. LCMS (ES+) 469.1 (M+ Na), RT 4.62 minutes {Method ).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; WO2009/71895; (2009); A1;,
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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-amino-3-iodobenzoate

A combined suspension of methyl 4-amino-3-iodobenzoate (2.0 g, 7.22 mmol), copper (_) iodide (28 mg, 0.14 mmol), bis(triphenylphosphine)palladium(II) dichloride (101 mg, 0.14 mmol), and 1-ethyl-4-ethynylbenzene (1.22 mL, 8.66 mmol) were stirred in toluene and TEA (1/1, 60 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 (5/1, v/v) to obtain the compound 45 as a white solid (2.02 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 8.07 (d, J = 2.0 Hz, 1H), 7.78 (dd, J = 8.6, 2.1 Hz, 1H), 7.41 (d, J = 8.2 Hz, 2H), 7.12 (d, J = 8.2 Hz, 2H), 6.64 (d, J = 8.6 Hz, 1H), 4.86 (s, 2H), 3.81 (s, 3H), 2.6 (q, J = 7.6 Hz, 2H), 1.19 (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) _ 166.6, 151.7, 144.8, 134.1, 131.3, 131.1, 127.9, 119.8, 118.8, 113.1, 107.1, 95.2, 84.1, 51.6, 28.7, 15.2.

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

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

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., Product Details of 19718-49-1

A combined suspension of methyl 4-amino-3-iodobenzoate (2,72 g, 9.83 mmol), copper (_) iodide (37 mg, 0.20 mmol), bis(triphenylphosphine)palladium(II) dichloride (138 mg, 0.20 mmol), and tert-butyl((4-ethynylbenzyl)oxy)dimethylsilane (2.91 g, 11.79 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 (7/1, v/v) to obtain the compound 62 as a brown solid (3.89 g, quant. yield):

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; 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

Related Products 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.

Preparation Example F-1. 3-Acetyl-4-amino-benzoic acid methyl ester To a solution of 4-amino-3-iodo-benzoic acid methyl ester (11.30g, 40.77mmol) in toluene (300mL) were added tributyl(1-ethoxyvinyl)tin (16.5mL, 48.9mmol) and tetrakis(triphenylphosphine)palladium(0) (9422mg, 8.154mmol) under nitrogen atmosphere, and the solution was stirred at 105C for 7 hours. After cooling to room temperature, water was added, the mixture was extracted with ethyl acetate-tetrahydrofuran, the organic layer was washed with water, and then, evaporated. The residue was dissolved in 280mL of tetrahydrofuran, 2N hydrochloric acid (80mL) was added thereto, followed by stirring for 3 hours at room temperature. The reaction mixture was cooled on an ice bath, an aqueous solution of 2N sodium hydroxide (80mL) was added, an aqueous solution of saturated sodium bicarbonate was further added, and the solution was extracted with ethyl acetate. An aqueous solution of 10% potassium fluoride was added to the organic layer, and the solution was stirred for 3 hours at room temperature. The organic layer was separated, washed with brine, then evaporated, the residue was purified by silica gel column chromatography (hexane-ethyl acetate), and title compound (6.42g, 33.2mmol, 81.4%) was obtained. 1H-NMR Spectrum (CDCl3) delta (ppm): 2.64 (3H, s), 3.89 (3H, s), 6.63 (1H, d, J=8.8Hz), 7.91 (1 H, dd, J=2.0, 8.8Hz), 8.47 (1 H, d, J=2.0Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-iodobenzoate, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application 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 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 100C. 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; Aventis Pharma Deutschland GmbH; EP1479677; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 19718-49-1, 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. 19718-49-1 name is Methyl 4-amino-3-iodobenzoate, 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.

A solution of methyl 4-amino-3-iodobenzoate (100 mg,0.36 mmol) and triethylamine (101 mu, 0.72 mmol) in DCM (3 ml) was added dropwise to a cooled (0 C) solution of trifluoroacetic acid anhydride (127 mu, 0.90 mmol) in DCM (1 ml). The cooling bath was removed and the mixture was stirred for 1.5 h. The crude product was poured into cold water and DCM was added. The phases were separated; solvents were removed in vacuo and the crude product taken to the next step without further purification. Yield: 129 mg (96%); white solid. MS (ESI+) m z 374 [M+H]+. HPLC purity: 96%. 1H NMR (600 MHz, CDC13) delta ppm 8.51 (d, J=1.83 Hz, 1 H) 8.47 (br. s., 1 H) 8.36 (d, J=8.54 Hz, 1 H) 8.08 (dd, J=8.85, 1.83 Hz, 1 H) 3.93 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-iodobenzoate, and friends who are interested can also refer to it.