Tag: M.W=200-300

These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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. 54314-84-0

Example 25; 5-{(lJ?)-2-[({l-[3-(Benzyloxy)propyl]-4-hydroxypiperidin-4-yl}methyl)amino]-l- hydroxyethyl}-8-hydroxyquinoin-2(lJH)-one; i) l-(3-Benzyloxy-propyl)-piperidin-4-oneA suspension of benzyl 3-bromo-propyl ether (2.29g), 4-piperidinone hydrate hydrochloride (1.69g), potassium carbonate (anhydrous) (3.45g) and potassium iodide (830mg) were stirred in dry DMF (40ml) at 85¡ãC and continued for 24 h. The reaction was poured into water (200 mL plus brine 25 mL) and extracted with EtOAc. The organic extract was evaporated and the residue was chromatographed on silica gel eluting with 4:3 EtOAc/isohexane giving the sub-titled compound as a colourless oil. Yield: 1.8g 1U NMR (300Mz, CDCl3) delta 7.39 – 7.32 (4H, m), 7.31 – 7.25 (IH, m), 4.52 (2H, d), 3.60 – 3.53 (2H, m), 2.79 – 2.70 (4H, m), 2.61 – 2.54 (2H, m), 2.48 – 2.41 (4H, m), 1.89 – 1.80 (2H, m)

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 54314-84-0.

Reference:
Patent; ASTRAZENECA AB; WO2007/102771; (2007); A1;,
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The chemical industry reduces the impact on the environment during synthesis 588-96-5, name is p-Bromophenetole, I believe this compound will play a more active role in future production and life. 588-96-5

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

The chemical industry reduces the impact on the environment during synthesis 588-96-5. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
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103291-07-2, 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below.

To a solution 5-bromo-2-fluoroanisole (109 g, 0.54 mol), ZnF2 (2.52 g, 24.39 mmol), Pd(dba)2 (3.08 g, 5.35 mmol), and P^Bu3 (5.2 mL of a 50% solution in toluene, 11 mmol) in DMF (1 L) was added trimethylsilyl methyl ketene acetal (121 g, 0.7 mol). The reaction mixture was stirred at 80-90 0C for 5 h under nitrogen atmosphere and then was allowed to cool to room temperature and diluted with EtOAc. The reaction mixture was filtered through Celite. The filtrate was washed with H2O (2 L) and the aqueous layer was extracted with EtOAc (2.5 L). The combined extracts were washed with brine (2 L x 2), dried over MgSO4, and concentrated at reduced pressure to give methyl 2-(4-fluoro-3- methoxyphenyl)-2-methylpropanoate (151 g), which was used for the next step without further purification. 1U NMR (400MHz, CDCl3): delta 7.04-6.98 (m, IH), 6.95-6.92 (dd, IH), 6.88-6.85 (m, IH), 3.89 (s, 3H), 3.67 (s, 3H), 1.57 (s, 6H).

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; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
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402-07-3,Some common heterocyclic compound, 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, molecular formula is C8H6BrF3O, 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.

Synthesis of (2-(Hydroxy(2-methoxy-4-(trifluoromethyl)phenyl)methyl)- 1 ‘-tosyl-l – 1 ,3 ‘- bipyrrol-2’-yl)(2-methoxy-4-(trifluoromethyl)phenyl)methanone (37). To a solution of l-bromo-2-methoxy-4-(trifiuoromethyl)benzene (720 mg, 2.88 mmol) in dry THF (5 mL) at -78 C under N2 was slowly added n-BuLi (1.15 mL, 2.5 M in n-pentane, 2.88 mmol). After being stirred for 30 min, a solution of 36 (550 mg, 1.06 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4C1 (15 mL) solution and extracted with EtO Ac (10 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtO Ac/petroleum) to give 37 (400 mg, 54% yield) as a light yellow solid. 1H NMR (400 MHz, CDCI3) delta 2.44 (s, 3H), 3.59 (br s, 3H), 3.84 (s, 3H), 5.77 (br s, 1H), 6.17-6.32 (m, 3H), 6.49 (br s, 1H), 6.70 (br s, 1H), 6.83 (d, J= 7.6 Hz, 1H), 7.13 (br s, 1H), 7.21 (br s, 1H), 7.35-7.37 (m, 4H), 7.42 (d, J= 2.8 Hz, 1H), 7.92 (d, J= 8.0 Hz, 2H) ppm; 13C NMR (CDC13, 100 MHz) delta 21.67, 55.75, 55.88, 67.96, 105.60, 105.64, 108.13, 108.03, 111.28, 116.78, 116.78, 116.78, 120.85, 120.85, 124.97, 126.20, 127.10, 127.30, 127.63, 127.63, 129.14, 129.14, 129.98, 129.98, 132.50, 132.56, 133.21, 133.45, 135.92, 145.38, 155.48, 157.01, 180.50 ppm; IR (KBr) 3444, 3137, 2923, 1668, 1562, 1447, 1361, 1180, 1014, 752, 668 cm”1.

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-3-methoxybenzotrifluoride, its application will become more common.

Reference:
Patent; CHONGQING ZEIN PHARMACEUTICAL CO., LTD.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; QIN, Yong; CHENG, Chunwei; SONG, Hao; LI, Rongshi; LIU, Yan; WO2014/116634; (2014); A1;,
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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. 450-88-4 name is 1-Bromo-4-fluoro-2-methoxybenzene, 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. 450-88-4

Intermediate Example Int20.014-(4-bromo-3-methoxyphenoxy)-1 -methylpiperidine To a stirred suspension of sodium hydride (1.76 g; 60% w/w sodium hydride in oil) in DMF (55 mL) was added 1 -methylpiperidin-4-ol (3.37 g) at 0 C. The mixture was stirred at room temperature for 30 minutes. 1 -bromo-4-fluoro-2- methoxybenzene (3.0 g) was added and the mixture was stirred at 100 C for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica- gel chromatography gave 3.65 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
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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. 583-19-7, name is 1-Bromo-2-ethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., 583-19-7

3-(2-bromoacetyl)-8-chloro-2H-chromen-2-one (150 mg, 0.54 mmol) and l-bromo-2-ethoxybenzene (108 mg, 0.54 mmol) were reacted in a microwave in the presence of CS2CO3 (528 mg, 1.62 mmol), Pd2(dba)3 (40mg, 0.054mmol.), xantphose (60mg, 0.108mmol), and dioxane (2 mL) at 160C for 15 minutes. The resulting product was then purified by pre-HPLC to yield 8-chloro-3-(2-(2-ethoxyphenylamino)thiazol-4-yl)-2H-chromen-2-one (20 mg, 10%) as a yellow solid. ESI-MS (EI+, m/z): 399.1 [M+l]+; 1HNMR (500 MHz, DMSO-<): delta 1.40 (t, J = 7 Hz, 3H), 4.14 (q, J= 7 Hz, 2H), 6.99-7.05 (m, 3H), 7.39 (t, J = 8 Hz, 1H), 7.76-7.79 (m, 2H), 7.93 (t, J= 7 Hz, 1H), 8.48-8.49 (m, 1H), 8.65 (s, 1H), 9.54 (s, 1H). 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:
Patent; DISCOVERYBIOMED, INC.; SCHWIEBERT, Erik; STREIFF, John; DIXON, John; GAO, Hongwu; WO2014/152213; (2014); A2;,
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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. 21702-84-1 name is 2,4-Dibromo-1-methoxybenzene, 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. 21702-84-1

(ii) 4-Methoxgammaisophthalonitrile 2,4-Dibromo-l -methoxybenzene (25 g, 0.094 mol; see step (i) above) was dissolved in dry DMF (50 mL). CuCN (25.3 g, 0.283 mol) was then added and the resulting mixture was stirred at 120C for 15 h, before being cooled to RT. The crude mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 25% ethyl acetate in petroleum ether as eluent, to yield the sub-title compound (7.1 g, 24%) as pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dibromo-1-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/135316; (2006); A1;,
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A common compound: 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54314-84-0

PREPARATION 5 [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[4-(3-benzyloxypropoxy)benzoyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate Scheme I, Step D: To a 0.5 L stirred round bottom, purged with nitrogen, charge in order: [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-(4-hydroxybenzoyl)-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (13.58 mmol), acetonitrile (250 mL), and potassium carbonate (67.92 mmol). To this stirred solution, at room temperature, add 3-bromopropoxymethylbenzene (27.2 mmol) and heat at 60¡ã C. for 16 hours under nitrogen. Dilute with EtOAc (200 mL) and filter. Concentrate the filtrate and purify by flash chromatography (330 g silica gel) eluting with 2-40percent EtOAc/chloroform. Concentrate the product containing fractions to give the title compound (9.0 g. 90.79percent): mass spectrum (m/z): 730.4 (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, 54314-84-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FIELDS, Todd; US2015/126469; (2015); A1;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 103291-07-2

Example 41i 1-(3-Bromophenyl)-4-fluoro-1-(4-fluoro-3-methoxyphenyl)-1H-isoindol-3-amine tert-Butyllithium (3.68 mL, 5.89 mmol) was added dropwise to THF (10 mL) at -100 C. under an argon atmosphere. A solution of 4-bromo-1-fluoro-2-methoxybenzene (0.604 g, 2.95 mmol) in THF (5 ml) was added dropwise followed by the addition of (E)-N-((3-bromophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (1 g, 2.46 mmol) in THF (5 ml). The resulting reaction mixture was left on the thawing cooling bath for 30 min then the cooling bath was removed and the mixture was stirred at r.t. for 1 h. Hydrogen chloride-methanol solution (11.78 mL, 14.73 mmol) was added and the resulting mixture was stirred at r.t. for 1 h. The mixture was concentrated and purified on a silica gel column eluding with 0-10% 0.1 M NH3 in MeOH in DCM to afford 0.98 g (93%) of the title compound. MS (ES+) m/z 429, 431 (M+H)+

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
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2859-78-1, name is 4-Bromo-1,2-dimethoxybenzene, belongs to ethers-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. 2859-78-1

General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 muL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).

Statistics shows that 2859-78-1 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-1,2-dimethoxybenzene.

Reference:
Article; Maibunkaew, Tapanee; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Bunrit, Anon; Ruchirawat, Somsak; Synlett; vol. 25; 12; (2014); p. 1769 – 1775;,
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