Month: June 2021

Electric Literature of 112734-22-2,Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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 ethyl 2-(4-cyano-2,6-difluorophenoxy)-4-formylnicotinate (0.30 g) obtained in Reference Example 229 and (4-bromo-2-fluorophenyl)methanamine (0.20 g) in THF (6 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, to a solution of the residue in acetic acid (6 mL) was added sodium triacetoxyhydroborate (0.29 g) at room temperature, and the mixture was stirred under an argon atmosphere at room temperature for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a solution of the obtained 4-((2-(4-bromo-2-fluorobenzyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yl)oxy)-3,5-difluorobenzonitrile (0.20 g), ((1-methyl-1H-pyrazol-4-yl)boronic acid (0.058 g) and 2M aqueous sodium carbonate solution (0.63 mL) in DME (4 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.031 g), and the mixture was stirred under an argon atmosphere at 80C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and solidified with ethyl acetate to give the title compound (0.017 g). MS: [M+H]+ 476.1 1H NMR (300 MHz, CDCl3) delta 3.96 (3H, s), 4.45 (2H, s), 4.86 (2H, s), 7.16-7.20 (1H, m), 7.22 (1H, d, J = 4.2 Hz), 7.26 (1H, brs), 7.36 (2H, d, J = 6.6 Hz), 7.40-7.47 (1H, m), 7.62 (1H, s), 7.74 (1H, s), 8.16 (1H, d, J = 5.1Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Bromo-2-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

8-bromo-4,5-dimethylquinoline, monohydrochloride (A): At 23 C, a 2-neck500 mL round-bottom flask equipped with magnetic stuffing bar, reflux condenser, and bubbler was flushed with N2 for several minutes. The flask was placed in a bath ofaluminum beads and charged with 12 N aq. HC1 (180 mL). Molten 2-bromo-5-methyl benzenamine (50.0 g, 0.270 mol) was added steadily to the flask while the aluminum bead bath was at 23 C. Once addition ensued, an off-white chunky precipitate formed. A glass stirring rod was periodically used to pulverize the chunks. Once addition was complete, the reaction was a suspension with particulate white solid in yellow liquid.At this point, a pressure-equalizing addition funnel was attached to the flask and charged with Methyl Vinyl Ketone (26.8 mL, 0.322 mol). The reaction was heated to 120 C under N2. A circulating chiller was applied to through the reflux condenser. The bubbler was then removed and a stream of air was passed steadily over the reaction while the Methyl Vinyl Ketone was added dropwise over 10 mm. Heating wascontinued for another 30 mm, then the air stream was cut. The reaction was refitted with the bubbler and an N2 stream was applied as the reaction was cooled to 23 C. The reaction was poured into THF (1.0 L) and the sluffy was cooled to – 20 C overnight. The precipitate was collected in a Buchner funnel on filter paper and washed with 2 x 100 mL of ice-cold THF. This afforded 8-bromo-4,5-dimethylquinoline,monohydrochioride. The material was immediately used in the reaction below. LCMSESI Calc?d for C11H10BrN (M+H): 236.0 / 238.0. Found 236.1 / 238.1 (M+H)

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; MCFADDEN, Ryan; MITCHELL, Michael, L.; WO2015/179448; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4101-68-2,Some common heterocyclic compound, 4101-68-2, name is 1,10-Dibromodecan, molecular formula is C10H20Br2, 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.

To a suspension of phthalimide potassium salt (5.57 g, 30 mmol) and K2CO3 (15.00 g, 100 mmol) in CH3CN (100 mL) was added1,10-dibromodecane (49.94 g, 185 mmol), then the mixture was refluxed for 11 hours. The obtained mixture was filtered and CH3CN was removed by a rotary evaporator. The crude product was purified by column chromatography (SiO2, PE/EA = 6 : 1) to give a whitesolid (10.19 g, 93 %).

The synthetic route of 4101-68-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Mengjun; Du, Xusheng; Tian, Huasheng; Jia, Qiong; Deng, Rong; Cui, Yahan; Wang, Chunyu; Meguellati, Kamel; Chinese Chemical Letters; vol. 30; 2; (2019); p. 345 – 348;,
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. 591-19-5, name is 3-Bromoaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6BrN

c. 3,4-Dibromoaniline. 3-Bromoaniline (3 g, 17.4 mmol) was dissolved in 15 ml CH2 Cl2 and the reaction mixture was cooled to -10 C. in an ice-salt bath. 2,4,4,6-Tetrabromo-2,5-cyclohexadienone, (9.29 g, 0.02 mmol) was added in small portions with constant stiting. The reaction mixture was stirred for a period of 7 hours at 0 C. after which the reaction was quenched with 2N NaOH (10 ml). The aqueous layer was extracted with CH2 Cl2 and the organic layer was dried over anhydrous Na2 SO4. The CH2 Cl2 layer was concentrated in vacuo and purified by column chromatography. Elution with 0-3% ethyl acetate/n-hexanes yielded 3.2 g (12.7 mmol, 73%) of pure product; mp 80-81 C.; IR (KBr) 3406, 3318, 3210, 1583, 1464, 1287, 1108, 860, 668; 1 H NMR (CDCl3) 6 6.49 (dd,1H,J=2.7,8.6), 6.7 (d,1H,J=2.64), 7.32 (d,1H,J=8.6); 13 C NMR (CDCl3) 6 112.6, 116, 120.1, 125.45, 134.26, 147.08.

The synthetic route of 591-19-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rutgers, The State University of New Jersey; US6063801; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 103-64-0, A common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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 round-bottom flask was charged with phenylacetylene (0.75 mmol, 0.08 mL), K2CO3 (0.75 mmol, 100 mg), PEG 200 (1 mL), and aryl halide (0.5 mmol). To this mixture, Pd(0) nano-catalyst supported on SDPP (1.5 mol-%, 3.0 mg) prepared according to our previous report [13] was added. In the case of aryl iodides and activated aryl bromides, the reaction mixture was placed in a 100 C oil bath; and in the case of the less active and deactivated aryl bromides and chlorides, the reaction mixture was placed in a 120 C oil bath. After completion of the reaction, the catalyst was removed by centrifugation and the remaining mixture was extracted with ethyl acetate (310 mL) and water several times and dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure, and then purified by column chromatography over silica gel 60 (230-240 mesh; Merck) using petroleum ether/ethyl acetate (5 : 1) as eluent to afford the product with high purity in 51-95% yield. Note: This procedure can also be used, but the catalyst is prepared in situ by adding the appropriate amounts of SDPP and Pd(OAc)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:
Article; Iranpoor, Nasser; Firouzabadi, Habib; Motevalli, Somayeh; Rajabi, Khashayar; Australian Journal of Chemistry; vol. 68; 6; (2015); p. 926 – 930;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)aniline

3-bromo-5-trifluoromethylaniline (48 g, 0.2 mol) was added to a three-necked flask equipped with argon,4-methylimidazole (19.7 g, 0.24 mol), cuprous iodide (5.7 g, 0.03 mol)8-hydroxyquinoline (4.4 g, 0.03 mol)(30g, 0.22mol) and 300ml of DMSO, stirred and heated to 120 C for 24 h, followed by TLC. After the reaction was completed, the mixture was cooled to 50 C. 200 ml of 14% aqueous ammonia was added and stirring was continued for 1 h. Water and ethyl acetate were extracted three times. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and the solvent was removed by rotary distillation.Then, the solvent was cooled in a refrigerator, and the precipitated crystals were filtered and dried to obtain 33.7 g of pale green needle-like crystals in a yield of 70%.

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 54962-75-3.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; Wang Jianping; Wang Jianguo; (14 pag.)CN107226809; (2017); A;,
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. 615-59-8, name is 1,4-Dibromo-2-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 615-59-8

(1) 2,5-dibromotoluene (10 mmol, 2.5 g), 4-methoxycarbonylbenzeneboronic acid (24 mmol, 4.33 g) under N2 protection.caesium fluoride (40 mmol, 6.0 g) was placed in a 250 mL three-necked flask, and 5% (1.2 to 2.0 g) of Pd (PPh3) catalyst was added.100 mL of anhydrous THF was used as a solvent, and refluxed at 67 C.After completion of the reaction, the product was isolated by silica gel column chromatography (petroleum ether, dichloromethane) to give a pink solid 2.91 g, yield 81%.

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; Shandong Normal University; Dong Yubin; Wang Jiancheng; Liu Congxue; Hu Yuhong; (14 pag.)CN108640906; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 58971-11-2, name is 3-Bromophenethylamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H10BrN

To a mixture of 2-(3-bromophenyl)ethanamine (485 mg, 2.42 mmol) and K2CO3 (469 mg, 3.39 mmol) in acetonitrile (7.3 mL) was added 1-bromo-2-methoxyethane (228 muL, 2.42 mmol), and the mixture was stirred ON at rt. The mixture was then heated at reflux for 6 h. An additional portion of 1-bromo-2-methoxyethane (75 muL, 0.80 mmol) was added, and heating was continued ON. The reaction mixture was filtered. The filtrate was concentrated, and residue purified by flash chromatography to provide 37A (189 mg, 30.2%). MS(ESI) m/z 257.9 (M+H).

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne M.; KICK, Ellen K.; VALENTE, Meriah Neissel; HU, Carol Hui; HALPERN, Oz Scott; JUSUF, Sutjano; (133 pag.)WO2018/5336; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10485-09-3, These common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, 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.

(Comparative Example 3) 1.2 ml of a tetrahydrofuran solution of 0.25 g of magnesium was cooled to 0C, and 5.0 ml of a tetrahydrofuran solution of 1.0 g of 2-bromoindene was slowly dropped thereto.After the dropping, the mixture was stirred at the same temperature for 1 hour, and 0.57 g of 2,6- dimethylbenzaldehyde was added thereto, and stirred for 12 hours while the temperature was being raised to 25C.After the confirmation of the degree of reaction progress by TLC, the reaction was terminated with an ammonium chloride aqueous solution, and an organic phase was extracted with ethyl acetate.[0132] After the obtained organic phase was dried with anhydrous magnesium sulfate, the organic phase was concentrated and purified by column chromatography. Then, 5 g of manganese dioxide was added to 30 ml of a chloroform solution of the obtained intermediate compound, and the mixture was stirred at 25 C for 12 hours. After the confirmation of the degree of reaction progress by TLC, the manganese dioxide was filtered, and 0.42 g (yield: 40%) of Comparative Product 3 shown below was obtained by recrystallization. Thestructure of Comparative Product 3 was confirmed by 1HNMR. 1H-NMR (CDC13; TMS) : delta 2.21 (s, 6H) , 3.85 (s, 2H) , 7.07 (d, 2H) , 7.20-7.26 (m, 2H) , 7.33-7.41 (m, 2H) , 7.47 (d, 1H) , 7.58 (d, 1H)

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANON KABUSHIKI KAISHA; SAITOH, Terunobu; WO2011/81078; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 4101-68-2 as follows. name: 1,10-Dibromodecan

2.2.4 9-(10-bromodecyl)-9H-carbazole (4) Under argon atmosphere, carbazole (1.67 g, 0.01 mol), anhydrous potassium carbonate (2.77 g, 0.02 mol), and 1,10-dibromodecane (6.00 g, 0.02 mol) in 40 mL of anhydrous acetonitrile were refluxed at 95 C for 36 h. After cooling to room temperature, insoluble substance was filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel with petroleum to get 9-(10-bromodecyl)-9H-carbazole as white crystals (1.66 g, Yield 43%). 1H NMR (500 MHz, CDCl3, delta): 8.08 (d, J = 7.7 Hz, 2H, Ar-H), 7.43 (t, J = 7.8 Hz, 2H, Ar-H), 7.35 (d, J = 8.1 Hz, 2H, Ar-H), 7.20 (t, J = 7.5 Hz, 2H, Ar-H), 4.21 (t, J = 7.3 Hz, 2H, CH2), 3.33 (t, J = 6.8 Hz, 2H, CH2Br), 1.79 (m, 4H, CH2), 1.33-0.91 (m, 12H, CH2). FT-IR (cm-1, KBr): 2930, 2850 (s; CH), 1632, 1619, 1593 (m; Ar). Anal. Calcd. For C22H28BrN: C, 68.39; H, 7.30; N, 3.63; Found: C, 68.47; H, 7.25; N, 3.56.

According to the analysis of related databases, 4101-68-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Jin; Wang, Weina; Gu, Jiangjiang; Li, Weizhi; Zhang, Qiuhong; Ding, Yin; Xi, Kai; Zheng, Youxuan; Jia, Xudong; Polymer; vol. 55; 26; (2014); p. 6696 – 6707;,
Bromide – Wikipedia,
bromide – Wiktionary