Tag: M.W=200-300

These common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, 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. HPLC of Formula: C8H10BrN

General procedure: Amine (0.25 mmol), and bromide (0.25 mmol) were taken up in acetonitrile (0.3 mL) in a conical vial equipped with a stirrer bar. Potassium carbonate (0.5 mmol) was added followed by potassium iodide (10 mol%) if required. The vial was sealed with a screwcap and the reaction was stirred at 40 C until thin layer chromatography (TLC) indicated complete consumption of the starting materials. A precipitate was formed during the reaction which was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography and sent to the Netherlands Cancer Institute (NKI) for biological testing.

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Milne, Kirsty; Sun, Jianhui; Zaal, Esther A.; Mowat, Jenna; Celie, Patrick H.N.; Fish, Alexander; Berkers, Celia R.; Forlani, Giuseppe; Loayza-Puch, Fabricio; Jamieson, Craig; Agami, Reuven; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2626 – 2631;,
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Related Products of 51554-93-9, These common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, 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.

Phenothiazine (2.37 g, 11.9 mmol), 1-bromo-4-n-octyl-benzene (4.17 g, 15.4 mmol) and sodium tert-butoxide (2.3 g, 23.8 mmol) are dissolved sufficiently in 50 mL of toluene.Tri tert-butylphosphine(0.144 g, 0.7 mmol)And Pd2 (dba) 3 (0.54 g, 0.59 mmol)After sufficiently dissolving at room temperature under a nitrogen atmosphere,And the mixture is stirred at 120 C under reflux.When the reaction is complete, work-up is carried out with a 1: 1 mixture of water and chloroform.After separating the organic layer after the work-up process using the extraction method,The solvent is removed under reduced pressure.After the solvent was removed, the product was recrystallized several times with methanol to obtain a pale yellow solid product (3.5 g, 76%) was obtained.

The synthetic route of 51554-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daegu Gyeongbuk Institute of Science and Technology Foundation; Jo, Hyo Jung; Kang, Jin Kyu; Nam, Jung Eun; Kim, Dae Hwan; (11 pag.)KR101526327; (2015); B1;,
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Application of 89359-54-6,Some common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, molecular formula is C9H17Br, 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 1 This example illustrates the synthesis of several compounds that are used as intermediates for the synthesis of other compounds. 1-(8,9-Oxidononyl)-3,7-dimethylxanthine was synthesised as follows: A mixture of theobromine (17.64 g, 98 mmol) and sodium hydride (2.35 g, 98 mmol) in dimethylsulfoxide (250 ml) was stirred for 15 minutes. 9-Bromo-1-nonene (20.0 g, 98 mmol) was added and stirring continued for 3 days. The reaction mixture was poured into water (300 ml) and extracted with dichloromethane (4*200 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (2*150 ml), dried over sodium sulfate, and the solvents evaporated under vacuum. The residue was crystallized (dichloromethane-ether) to give 1-(8-nonenyl)-3,7-dimethylxanthine (24.34 g, 99% yield) as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 9-Bromo-1-nonene, its application will become more common.

Reference:
Patent; Cell Therapeutics, Inc.; US5641783; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 89359-54-6, name is 9-Bromo-1-nonene, 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 89359-54-6, Product Details of 89359-54-6

General procedure: 4.3.1. ((oct-7-en-1-yloxy)methyl)cyclohexane (H1)To a stirred solution of cyclohexylmethanol (6) (492 muL, 4.0 mmol,2 eq) in DMF (7 mL) under argon was added NaH (60% suspension inmineral oil; 160 mg, 4.0 mmol, 2 eq) at 0 C. The suspension was stirredat 0 C for 30 min, then 8-bromodec-1-octene (7) (336 muL, 2.0 mmol,1 eq) was added dropwise to the mixture. The mixture was allowed towarm to room temperature and stirred for 1 h. After the reaction wasquenched with saturated NH4Cl, the whole was extracted with Et2O.The extract was washed with H2O and brine, then dried over MgSO4.The filtrate was concentrated under reduced pressure to give an oilyresidue, which was purified using silica gel chromatography (petroleum ether_EtOAc=40:1) to afford H1 (341 mg, 76% yield) as a colorless oil.

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; Yang, Haoran; Li, Ying; Chai, Huining; Yakura, Takayuki; Liu, Bo; Yao, Qingqiang; Bioorganic Chemistry; vol. 98; (2020);,
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Reference of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Dimethylamino-2H-isoquinolin-l-one (50mg, 0.27mmol), cuprous iodide (lOmg, 0.053mmol), and potassium carbonate (37mg, 0.27mmol) were deposited in sealed vessel. 3mL DMSO and 2,6-dibromotoluene (133mg, 0.532mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 1500C for 5 hours. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (30% ethyl acetate/hexanes) to yield 2-(3-Bromo-2-methyl-phenyl)-6-dimethyl- amino-2H-isoquinolin-l-one (43mg, 0.12mmol). MS (ESI) 357 (M+H)+.

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, 2,6-Dibromotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/98144; (2009); A1;,
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Synthetic Route of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

(0104) Firstly, 18.96 g (0.08 mol) of Compound 1 (5-Bromo-2,2-difluorobenzodioxol), 1.52 g (0.008 mol) of CuI, 26.88 g (0.48 mol) of KOH, 200 mL of polyethylene glycol (PEG 400), and 50 mL of water were added into a reaction bottle. Then, the mixture in the reaction bottle was heated to reflux under nitrogen for 48 hours. After the reaction completed, an extraction was performed by using ethyl acetate (EA)/sodium chloride aqueous solution. The organic phase of the extraction solution was collected and concentrated. A column chromatography was performed by using hexane/EA (hexane: EA=8:2) as a mobile phase. The mobile phase after column chromatography was concentrated by the rotary concentrator, and Compound 2 (light yellow liquid) was obtained. The reaction is as follows:

The synthetic route of 33070-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAXIN MATERIALS CORPORATION; LO, CHIH-YUAN; LIU, HSIN-CHENG; LAN, GUO-YU; WANG, CHUN-CHIH; (27 pag.)US2016/222295; (2016); A1;,
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Related Products of 3638-73-1, 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 3638-73-1 as follows.

Sodium nitrite (65.2 mmol) was added in several portions to a solution of 2,5-dibromobenzenamine (55.8 mmol) in trifluoroacetic acid (80 mL) at 0 C. The resulting solution was added to a boiling solution of sodium sulfate (10 g) in 50% sulfuric acid (120 mL) and the reaction mixture was maintained at reflux for 1 h. Then the product was steam-distilled and the distillate was extracted with dichloromethane (2*200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to provide 2,5-dibromophenol in 41% yield as a yellow solid.

According to the analysis of related databases, 3638-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/22581; (2010); A1;,
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Reference of 67567-26-4,Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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 solution of 1-tert-butoxycarbonyl-4-methyl-piperidine-4-carboxylic acid (240 mg, 0.99 mmol, 1.0 eq.) in CH2Cl2 (8.0 mL) was added pyridine (320 mg, 0.32 mL, 3.9 mmol, 4.0 eq.), (COCl)2 (130 mg, 0.088 mL, 0.99 mmol, 1.0 eq.) followed by 2 drops of DMF. After 1 h at room temperature, 4-bromo-2,6-difluoro-aniline (210 mg, 0.99 mmol, 1.0 eq.) was added and the mixture was stirred at room temperature overnight, after which CH2Cl2 was added and washed with water and brine. The organic layers were dried, evaporated and purified over silica gel with ethyl acetate in hexanes (5 to 50% gradient) to give tert-butyl 4-[(4-bromo-2,6-difluoro- phenyl)carbamoyl]-4-methyl-piperidine-1-carboxylate (350 mg, 82%). 1H NMR (CDCl3) d: 7.43 (s, 1H), 7.11 (d, J= 6.6 Hz, 2H), 3.65 – 3.81 (m, 2H), 3.14 – 3.22 (m, 2H), 2.09 (d, J= 13.9 Hz, 2H), 1.46 – 1.52 (m, 2H), 1.45 (s, 9H), 1.32 (s, 3H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
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73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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-(4-Bromophenyl)ethanamine

[000449] Synthesis of tert-butyl (4-bromophenethyl) carbamate (547): To a stirred solution of 2-(4-bromophenyl) ethan-1-amine 546 (500 mg, 2.50 mmol) in CH2C12 (5 mL) under argon atmosphere were added Boc-anhydride (594 mg, 2.75 mmol), diisopropyl ethyl amine (1 mL, 7.50 mmol) at RT and stirred for 4 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (25 mL) and extracted with CH2C12 (235 mL). The combined organic extracts were washed with water (25 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5-8% EtOAc/ hexanes to afford compound 547 (500 mg, 65%) as white solid. TLC: 10% EtOAc/ hexanes (R 0.5); 1H-NMR (DMSO-d6, 400 MHz): oe 7.46 (d, J= 8.0 Hz, 2H), 7.12 (d, J= 8.0 Hz, 2H), 6.86-6.82 (m, 1H), 3.12-3.08 (m, 2H), 2.68-2.64 (m, 2H), 1.32 (s, 9H).

The synthetic route of 73918-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Reference of 142808-15-9, These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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.

Place 4-bromo-2-fluorotrifluorotoluene (29.2 g, 120 mmol, 1 eq.) In a dropping funnel and set aside. Diisopropylamine (14.6g, 144mmol, 1.2eq.) And 220ml of tetrahydrofuran were added to the reaction flask, cooled to -78 C, and n-butyllithium (52.8ml, 132mmol, 1.1eq.) Was added dropwise under the protection of nitrogen. After the dropwise addition, the mixture was stirred at 25 C for 1 hour. Recool to -78 C and add 4-bromo-2-fluorotrifluorotoluene dropwise. After the dropwise addition, the mixture was stirred at -78 C for 2 hours. Iodomethane (18.7g, 132mmol, 1.1eq.) Was added dropwise, and the temperature was gradually raised to 25 C for 16 hours.[0058]After the reaction was completed, it was cooled in an ice water bath, and 150 ml of saturated ammonium chloride solution was added dropwise for quenching. It was extracted with ethyl acetate, and the organic phase was concentrated to obtain 26.8 g of yellow oily 1-bromo-3-fluoro-2-methyl-4- (trifluoromethyl) benzene in 87% yield. Used directly in the next step.

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; Ali Biological New Materials (Changzhou) Co., Ltd.; Shi Jianyun; Xu Yibo; Shi Hongliang; Dai Hongsheng; Zhang Jun; (6 pag.)CN110885290; (2020); A;,
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