Month: June 2021

Some common heterocyclic compound, 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H3BrN2S, 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. Computed Properties of C6H3BrN2S

5-bromobenzo[c][1,2,5]thiadiazole (5.00 g, 23.3 mmol), 2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (9.80 g, 34.9 mmol), potassium carbonate (8.03 g, 58.1 mmol), Dimethoxyethane (DME) (100 mL), and Water (25 mL) were combined in a flask. The solution was purged with nitrogen for 15 min then palladium tetrakis (1.34 g, 1.16 mmol) was added. The reaction was heated to reflux under nitrogen overnight. The reaction mixture was extracted with ethyl acetate (3 times), then washed with Brine and Water. The crude solid was purified with silica gel using 60/40 heptanes/Ethyl Acetate as the solvent system to afford a 4.70 g (70% yield) of a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1753-75-9, its application will become more common.

Reference:
Patent; Universal Display Corporation; BOUDREAULT, Pierre-Luc T.; ALLEYNE, Bert; XIA, Chuanjun; (154 pag.)US2018/13077; (2018); A1;,
Bromide – Wikipedia,
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These common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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. Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

To a stirred solution of 5-bromo-N1-methylbenzene-1,2-diamine (38 g, 189 mmol) in THF (800 mL) was added CDI (37 g, 228 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed for 16 h. The mixture was cooled to room temperature. The mixture was diluted with water (1 L) and stirred at room temperature for 30 min. The precipitated solids were collected by filtration and washed with water (200 mL). The filter cake was dried under vacuum to afford 6-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one (40 g, 93%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.02 (br s, 1H), 7.35 (d, J = 1.9 Hz, 1H), 7.14 (dd, J = 8.2, 1.9 Hz, 1H), 6.92 (d, J = 8.2 Hz, 1H), 3.27 (s, 3H). LC/MS (ESI, m/z): [(M + 1)]+ = 227.10, 229.10

The synthetic route of 5-Bromo-N1-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103273-01-4, These common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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: A mixture of 2-bromo-4-tert-butylaniline (2.28 g, 10 mmol), 2,5-dimethoxytetrahydrofuran (4.2 g, 30 mmol) and glacial acetic acid (150 mL) in a 250 mL three-necked RB flask was refluxed under nitrogen for 17 h. Then it was cooled, poured into aq. HCl (200 mL) and extracted with CH2Cl2, then combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was purified by column chromatography (PE) to afford 3ac as a white powder (1.97 g, 52 %); Rf = 0.28 (PE); m. p. 138 -140 C; 1H-NMR (CDCl3, 300 MHz) delta: 8.18 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 11.4 Hz, 1H), 7.55 (d, J = 10.8 Hz, 1H), 7.42 (m, 3H), 7.29 (m, 2H), 7.12 (d, J = 7.8 Hz, 2H), 1.45 (s, 9H); 13C-NMR (CDCl3, 100 MHz) delta: 153.85, 141.01, 133.88, 131.20, 130.45, 126.03, 125.89, 123.42, 123.20, 120.35, 119.89, 110.18, 36.06, 31.32.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromobenzo[c][1,2,5]thiadiazole

After reacting lithium diisopropylamide (LDA) with N-Boc-3-methylindole in tetrahydrofuran (THF) at -20 ° C.,Triisopropyl borate was added and reacted for 1.5 hours to obtain N-Boc-3-methylindole-2-boronic acid.As shown by the following formula (8), “Boc” represents a tert-butoxycarbonyl group.Next, without isolating the obtained boronic acid, in the presence of tetrakis (triphenylphosphine) palladium (20 molpercent),The reaction was allowed to proceed at 95 ° C. for 4 hours in a mixed solvent of 4-bromo-2,1,3-benzothiadiazole and dioxane / potassium carbonate aqueous solution to obtain an indolylbenzothiadiazole derivative 1a in a yield of 84percent

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; YOKOHAMA NATIONAL UNIVERSITY; ITO, SUGURU; ASAMI, MASATOSHI; YAMADA, TAKESHI; TAGUCHI, TOMOHIRO; (23 pag.)JP2017/57191; (2017); A;,
Bromide – Wikipedia,
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These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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. name: 3-Bromophenethylamine

General procedure: 4-[(Ethoxycarbonyl)amino]butanoic acid (12a, 700 mg, 4mmol) was dissolved in an hydrous dichloromethane (14 mL) under argon atmosphere. The solution was cooled to 0 C. Triethylamine (1.2 mL, 870 mg, 8.6 mmol) and 3-fluorophenethylamine (0.6 mL, 4.6 mmol) were added consecutively. Afterwards EDC-HCl (900 mg, 4.7 mmol)was added in one portion. Catalytic amount DMAP (30 mg)was added, the resulting mixture was stirred for 1 h at 0 C and then for 16 h at room temperature. The reaction mixture was diluted with dichloromethane (30 mL) and consecutively washed with 1M HCl, saturated NaHCO3 solution and water (20 mL of each). The combined extracts were dried (Na2SO4) and evaporated to give an oily residue.The crude product was crystallized from hexane

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

Reference:
Article; Ahamed, Muneer; Vermeulen, Koen; Schnekenburger, Michael; Moltzau, Lise Roman; Levy, Finn Olav; Marton, Janos; Froeyen, Mathy; Olberg, Dag Erlend; Diederich, Marc; Bormans, Guy; Letters in drug design and discovery; vol. 14; 7; (2017); p. 787 – 797;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1, name is 2-Bromo-4-fluoroaniline, belongs to bromides-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. Application In Synthesis of 2-Bromo-4-fluoroaniline

Example 25Synthesis of 2-Bromo-4-Fluoro-5-Nitroaniline2-Bromo-4-fluoroaniline (47.5 g, 250 mmol) was added to a solution of concentrated H2SO4 (300 mL) keeping the internal temperature below 30 C. The mixture was aged for ca. 30-60 minutes then cooled to -20 C. 90% HNO3 (35 g) was added dropwise over ca. 60 minutes keeping the internal temperature between -15 to -20 C. TLC indicated a slight amount of starting material, so a further aliquot of 90% HNO3 (3 g) was added over 5 minutes at -15 to -20 C. The cold mixture was then poured on to ice H2O (ca. 1 L ice+500 mL H2O) and EtOAc (1 L). The aqueous and organic layers were partitioned and the organic layer was washed with saturated NaHCO3 (2×500 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a dark solid (35 g, 60%).1H NMR (DMSO-d6, 300 MHz): delta 8.27 (br. S, 2H), 7.70 (d 1H), 7.47 (d, 1H); m/z=275.9 (M+MeCN+H)+ for 79Br.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha; US2011/130415; (2011); A1;,
Bromide – Wikipedia,
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Electric Literature of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

100 g of intermediate 2-1, 186 g of intermediate 1-2, 203 g of potassium carbonate, 23.7 g of tetrabutylammonium bromide (TBAB) were added to a 2 L three-necked flask, and 800 ml of toluene, 200 ml of ethanol, and 200 ml of water were successively added. Nitrogen gas was added, stirred for 15 min, 2.1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated to 80 C for refluxing for 8 hours. The TLC was used to monitor the reaction of the starting materials and then cooled to room temperature.The impurities were separated, and the organic phase was washed with water until neutral. After drying over anhydrous sodium sulfate, the residue was purified by silica gel column to obtain 107.9 g of intermediate 2 in a yield of 92.2%.

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; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Dandan; Tian Mi; He Haixiao; Li Jiangnan; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; (33 pag.)CN109535131; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-2-fluoroaniline

Under an argon atmosphere, 5-bromo-2-fluoro stirring by addition of water (120mL) to the aniline (45.6g, 240mmol) and, after the addition of concentrated hydrochloric acid (120mL), cooled to -20 , and sodium nitrite ( 19.9g, was added dropwise an aqueous solution of 288mmol) and water (80mL). After stirring 20 minutes at -20 ,Adding an aqueous solution of potassium iodide (59.8g, 360mmol) and water (60mL), andIt was stirred for 30 minutes. After extraction with hexane, the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, sodium sulfite solution and dried over sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatographyPurified5-Bromo-2-fluoro-iodobenzene (54.6g, 181mmol)(Yield: 76%).

According to the analysis of related databases, 2924-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Idemitsu Kosan Corporation; Hayama, Tomoharu; Kawamura, Masahiro; Mizuki, Yumiko; Ito, Hirokazu; Haketa, Tasuku; (50 pag.)KR2016/18458; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69038-76-2, name is 4-Bromo-N1-methylbenzene-1,2-diamine, belongs to bromides-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 69038-76-2, Quality Control of 4-Bromo-N1-methylbenzene-1,2-diamine

A mixture of 4-bromo-N1-methylbenzene-1,2-diamine (19) (250 mg, 1.2434 mmol, 1 equiv) and bisulfite adduct of benzaldehyde (392 mg, 1.8651 mmol, 1.5 equiv) in 4 mL DMF was stirred at 60?C for 4h. The reaction mixture was diluted with water and extracted with EA. The organic layer was dried, filtered and evaporated. The crude 20a (236.8 mg, 66.3% yield) was used in the next step without purification. Mp 147.6-149.9 C (150-152 C [13]). HRMS m/z calculated for C14H11N2Br [M+H]+ 287.0184, found: 287.0190. CAS No. 760212-73-5

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, 4-Bromo-N1-methylbenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cal??kan, Burcu; Banoglu, Erden; Guer Maz, Tu?ce; Nocentini, Alessio; Supuran, Claudiu T.; Uslu, Azize Gizem; Bioorganic Chemistry; vol. 95; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, 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. Formula: C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

The synthetic route of 4-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary