Category: 106896-49-5

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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H8BrNO2

To a 250 mL round-bottom flask was added methyl 4-amino-3-bromobenzoate 32a (2.4 g, 10.43 mmol, 1.00 equiv.), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane (2.6 g, 12.38 mmol, 1.20 equiv.), dioxane (100 mL), aq. sodium bicarbonate (37 mL, 3.50 equiv, 1M), and Pd(PPh3)4 (1.21 g, 1.05 mmol, 0.10 equiv.). The resulting mixture was heated at 100C overnight. After cooling to room temperature, the mixture was diluted with 300 mL of EA and washed with brine (200 mL x 2). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep- HPLC using the following conditions (IntelFlash-1): Column, silica gel; mobile phase, PE_EA=100:0 increasing to PE_EA=50:50 within 30 min; Detector, UV 254 nm. Removal of solvents afforded methyl 4-amino-3-(3,6-dihydro-2H-pyran-4-yl)benzoate 32b (2.4 g, 99% as a white solid.

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; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Synthetic Route of 106896-49-5,Some common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50% EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80%) as a colourless syrup.

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-bromobenzoate, its application will become more common.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, 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 106896-49-5

A flame-dried flask, equipped with a reflux condensor, containing methyl 4- amino-3-bromobenzoate (2.5 g, 10.87 mmol), bis(neopentyl glycolato)diboron (3.07 g, 13.58 mmol), potassium acetate (3.20 g, 32.6 mmol), and PdC^dppf -CH^C^ adduct(0.222 g, 0.272 mmol) was added degassed DMSO (31.0 mL). The resulting dark red- brown suspension was warmed to 85 C. After 2.5 h, the resulting dark black reaction was cooled to RT and poured into cold water (100 mL) to give a suspension. The suspension was extracted with EtOAc (3x). The combined organic layers were washed with sat. aHC03, brine, dried over sodium sulfate, filtered and concentrated to give a brown solid weighing 3.1 g. Purification by normal phase chromatography gave 1.64 g (55%) of Intermediate 39 as a pale, yellow solid. lH NMR (500 MHz, CDC13) delta ppm8.35 (d, J=2.20 Hz, 1 H), 7.84 (dd, J=8.53, 2.20 Hz, 1 H), 6.52 (d, J=8.53 Hz, 1 H), 5.25 (br. s., 2 H), 3.84 (s, 3 H), 3.79 (s, 4 H), 1.03 (s, 6 H). MS (ESI) m/z: 196.0 (M-C5H8+H)+

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James, R.; FANG, Tianan; DECICCO, Carl, P.; PINTO, Donald, J., P.; ROSSI, Karen, A.; HU, Zilun; JEON, Yoon; QUAN, Mimi, L.; SMALLHEER, Joanne, M.; WANG, Yufeng; YANG, Wu; WO2011/100401; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

To a 1L rmmd-boitom t1ask purged with and rnaintained under an inert atrnosphere of.5 nitrogen vvas added methyl 4-amino-3-bromobenzoate 249a (13.6 g, 59.12 mmol, 1.00equiv.), (furan-3-yl)boronic acid (10 g, 89.37 mmol, 1.50 equiv.), 1,4-dioxane (500 mL), 1Maq. NaHC01 (17.5 g, 3.50 equiv.), and tetrakis(triphenylphosphine) palladium (6.86 g, 5.94mmol, 0.10 equiv.). The resulting mixture was heated at ll (J”C overnight vvith stirring. Aftercooling to room temperature, the mixture was diluted with 200 mL of water, and extracted10 with ethy 1 acetate (500 mL x 2). The combined orga.nic extracts were washed successivelywith t-hO (500 mL) and brine (500 mL x 2), dried over anhydrous sodium sulfate, andconcentrated under vacuum The crude product was purified by Flash-Prep-HPLC using thefollowing conditions (lntelFlash-1 ): Colunm, silica gel; mobile phase: EA: PE=O: 100increasing toEA: PE'”50:50 within 20 min; Detector, UV 254 nm. Removal of sol vents gavel 5 methyl 4-amino-3-(furan-3-yl)benzoate 25 l a (8.345 g, 65%) as a yellow oil.

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-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, belongs to esters-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 106896-49-5, category: esters-buliding-blocks

To a 250 rnL rmmd bottom flask purged with and maintained under Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8BrNO2

Example 40 theta-Cyano^’-methoxy-biphenyl-S-carboxylic acid methyl esterStep 1Step 1 : Methyl 4-amino-3-bromo benzoate (0.5 g, 2.17 mmol) was dissolved in dry dichloromethane (5 ml.) and the solution was cooled to -100C. A solution of BF3-Et2O (0.41 ml, 3.26 mmol) followed by te/f-butyl nitrite (0.32 mL, 2.72 mmol) was added dropwise to the mixture. The very dense solution was allowed to reach room temperature and was then diluted with hexanes (10 mL). The resulting solid was collected by filtration and washed again with hexanes. This was rapidly transferred in a flask containing a solution of NaCN (0.32 g, 6.52 mmol) and CuCN (0.233g, 2.61 mmol) in H2O/toluene (2:1 ; 3 mL) at 5C and stirred at this temperature for 30 min.. The mixture was then allowed to reach room temperature and finally it was heated at 600C for a further 25 min. The solution was then cooled to room temperature and then partitioned between water (15 mL) and EtOAc (15 mL). The organic phase was washed with brine, dried (Na2SO4) a nd solvent was rem oved in vacuo. Recrystallisation from hexanes/EtOAc gave 3-bromo-4-cyano-benzoic acid methylester as a grey solid (0.213g, 41 %). 1H NMR (400 MHz, c/6-Acetone): 8.35 (1 H, d), 8.17 (1 H, dd), 8.05 (1 H, d), 3.97 (3H, s).

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 106896-49-5.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 106896-49-5, These common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, 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.

General procedure: An over-dried vial equipped with stir bar was charged with Pd(OAc)2 (0.0055 g, 0.0245mmol, 0.10 equiv.), dppb (0.020 g, 0.0489 mmol, 0.2 equiv.) and K2CO3 (0.15 g, 0.98 mmol, 4.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and the contents were allowed to stir. A second over-dried vial equipped with a stir bar was charged with cyclopropanol (0.05 g, 0.245 mmol, 1.0 equiv.) and 2-bromoaniline (0.084 g, 0.489 mmol, 2.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and contents allowed to stir. The solution of substrates was added to the solution containing the palladium catalyst. The reaction vial was purged with argon, capped with a rubber septum and heated to 110 C for 24hrs. Upon completion, the reaction mixture was filtered through a pad of celite using EtOAc, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with the indicated solvent mixture to afford the desired quinoline product. Purification by flash column chromatography using 20% EtOAc in hexanes provided the desired quinoline as a pale yellow oil (0.051 g, 0.19 mmol) in 76% yield

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nikolaev, Andrei; Nithiy, Nisha; Orellana, Arturo; Synlett; vol. 25; 16; (2014); p. 2301 – 2305;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 106896-49-5, A common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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.

Example 1c Preparation of 3-Bromo-4-cyano-benzoic acid methyl ester A solution of 4-Amino-3-bromo-benzoic acid methyl ester (1.00 g, 4.35 mmol) in dichloromethane (20 mL) is cooled to -10 C. and treated dropwise with 90% tert-butyl nitrite (0.58 g, 0.67 mL, 5.08 mmol) followed by boron trifluoride diethyl etherate (0.94 g, 0.81 mL, 6.62 mmol). The suspension is allowed to warm to room temperature and stirred for 4 h. Diethyl ether (20 mL) is added, and the off-white solid is collected by filtration, washed with diethyl ether and dried briefly under high vacuum. The solid is then suspended in toluene (15 mL) and cooled to 0 C. A solution of copper (I) cyanide (0.52 g, 5.8 mmol) and sodium cyanide (0.71 g, 14.5 mmol) in water (10 mL) is added dropwise over 10 min. The mixture is stirred at 0 C. for 30 min, allowed to warm to room temperature, and then heated to 60 C. After 1 h, the solids are completely dissolved. The mixture is allowed to cool to room temperature, and ethyl acetate (20 mL) and water (20 mL) are added. The aqueous layer is separated and extracted with ethyl acetate (2*20 mL). The organic layers are combined, washed with water (2*10 mL) and brine, dried over Na2SO4, filtered and concentrated at reduced pressure. The solid residue obtained is recrystallized from hexanes/ethyl acetate to afford 3-Bromo-4-cyano-benzoic acid methyl ester (0.42 g, 39%) as a tan solid. The recrystallization mother liquor is concentrated and chromatographed (Biotage, 95:5 to 85:15 hexanes/ethyl acetate) to afford an additional portion of 3-Bromo-4-cyano-benzoic acid methyl ester (0.34 g, total yield: 0.76 g, 73%).

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; US2008/119457; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 106896-49-5, 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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An over-dried vial equipped with stir bar was charged with Pd(OAc)2 (0.0055 g, 0.0245mmol, 0.10 equiv.), dppb (0.020 g, 0.0489 mmol, 0.2 equiv.) and K2CO3 (0.15 g, 0.98 mmol, 4.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and the contents were allowed to stir. A second over-dried vial equipped with a stir bar was charged with cyclopropanol (0.05 g, 0.245 mmol, 1.0 equiv.) and 2-bromoaniline (0.084 g, 0.489 mmol, 2.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and contents allowed to stir. The solution of substrates was added to the solution containing the palladium catalyst. The reaction vial was purged with argon, capped with a rubber septum and heated to 110 C for 24hrs. Upon completion, the reaction mixture was filtered through a pad of celite using EtOAc, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with the indicated solvent mixture to afford the desired quinoline product. Purification by flash column chromatography using 20% EtOAc in hexanes provided the desired quinoline as a pale yellow oil (0.051 g, 0.19 mmol) in 76% yield

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-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nikolaev, Andrei; Nithiy, Nisha; Orellana, Arturo; Synlett; vol. 25; 16; (2014); p. 2301 – 2305;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,

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-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; YALE UNIVERSITY; WO2008/70823; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics