Tag: M.W=200-300

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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8BrNO

General Procedure: Methyl 2-{[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}propanoate (7) (4 g, 13.0 mmol) was dissolved in pyridine (10 mL). After 5 min, 3-bromo-2-chloroaniline (3.22 g, 15.6 mmol) was added. The reaction was complete within a few hours. The reaction mixture was then extracted using diethyl ether. The combined organic phases were washed with 1N HCl and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

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; Evans, Karen A.; Shearer, Barry G.; Wisnoski, David D.; Shi, Dongchuan; Sparks, Steven M.; Sternbach, Daniel D.; Winegar, Deborah A.; Billin, Andrew N.; Britt, Christy; Way, James M.; Epperly, Andrea H.; Leesnitzer, Lisa M.; Merrihew, Raymond V.; Xu, Robert X.; Lambert, Millard H.; Jin, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2345 – 2350;,
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27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, 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. Quality Control of 1-Bromo-4-methoxy-2-methylbenzene

This experiment was carried out four times. Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-yl acetate (187 g, 1.87 mol), palladium(ll) acetate (7.5 g, 33 mmol) and tri-o-tolylphosphine (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 C for 18 hours. After it had cooled to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 C. The resulting mixture was diluted with toluene (500 mL) and filtered through diatomaceous earth; the filter pad was thoroughly washed with ethyl acetate (2 x 1 .5 L). The organic phase from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield: 602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.05 (d, J=8.3 Hz, 1 H), 6.70- 6.77 (m , 2H), 3.79 (s, 3H), 3.65 (s, 2H), 2.22 (s, 3H), 2.14 (s, 3H).

The synthetic route of 27060-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; GRAY, David Lawrence Firman; GREEN, Michael Eric; HENDERSON, Jaclyn Louise; LEE, Chewah; MENTE, Scot Richard; O’NEIL, Steven Victor; ROGERS, Bruce Nelsen; ZHANG, Lei; WO2014/207601; (2014); A1;,
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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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 6358-77-6

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 1.00 g, 4.95 mmol), 3-chloro-4-methylphenylboronic acid (Acros, 1.69 g, 9.90 mmol), 1,1 ‘-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.81 g, 0.99 mmol), and purged with nitrogen. 1,4-Dioxane (37.1 ml) and an aqueous sodium carbonate solution (1.9 M, 12.4 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-4′-methyl-[l,l’-bipheny 1]-3-amine (1.03 g, 4.16 mmol, 84.0 % yield) as a tan solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

The product of Example 33D (62 mg, 0.2 mmol) was treated with triethyl orthobenzoate (Aldrich, 0.5 mL) in DMF (1 mL) at 100° C. for 10 h. It was then concentrated. The title product was purified by preparative HPLC (Xterra.(TM)., column, Xterra RP-18, 5 mum, 30.x.100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (40.0 mg, 50percent). 1H NMR (500 MHz, CD3OD) delta 1.52-1.64 (m, 1 H), 1.68-1.80 (m, 1 H), 1.80-1.92 (m, 1 H), 2.06-2.18 (m, 1 H), 2.25-2.31 (m, 1 H), 2.75-3.10 (m, 5 H), 3.39-3.49 (m, 1 H), 5.14-5.27 (m, 1 H), 7.55-7.66 (m, 3 H), 7.69 (dd, J=8.5, 1.8 Hz, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.00 (d, J=1.5 Hz, 1 H), 8.27 (dd, J=8.1, 1.7 Hz, 2 H), 8.89 (s, 2 H) ppm; MS (DCl/NH3): 399 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Triethoxymethyl)benzene, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2005/137204; (2005); A1;,
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5905-69-1, These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)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.

(Reference Example 71) Ethyl 1-[4-(difluoromethoxy)phenyl]piperidine-4-carboxylate[0521] Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 muL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80C for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 – 90/10] to obtain the title compound (3.17 g, yield: 56%). [0523] 1H-NMR (400 MHz, CDCl3) delta: 7.07-7.00 (2H, m), 6.95-6.87 (2H, m), 6.41 (1H, t, J = 75 Hz), 4.16 (2H, q, J = 7 Hz), 3.61-3.55 (2H, m), 2.84-2.73 (2H, m), 2.47-2.39 (1H, m), 2.08-1.99 (2H, m), 1.95-1.83 (2H, m), 1.27 (3H, t, J = 7 Hz).

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 5905-69-1.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
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588-96-5, name is p-Bromophenetole, 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. Safety of p-Bromophenetole

Example XIV.1 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid 1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70 C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C22H27NO3 (M=353.5 g/mol) ESI-MS: 354 [M+H]+Rt (HPLC): 1.69 min (method C)

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (2013); A1;,
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Reference of 202865-80-3, 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. 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 5-amino-3-t-butyl-1-(4-chlorobenzyl)pyrazole (50.0 mg, 0.190 mmol) and dioxane (1 mL) were added 4-bromo-2-fluoro-1-isopropoxybenzene (49 mg, 0.21 mmol), tris(dibenzylideneacetone)(0) (2.2 mg, 0.0024 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.3 mg, 0.0057 mmol) and sodium phenoxide trihydrate (48 mg, 0.28 mmol), and the resulting mixture was stirred at 170C for 30 minutes under microwave irradiation. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed by brine, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) and reversed-phase HPLC (0.3%fomic acid/acetonitrile) to give 3-t-butyl-1-(4-chlorobenzyl)-5-(3-fluoro-4-isopropoxyphenylamino)pyrazole (33 mg, Yield: 42%) as pale yellow solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.20-1.24 (15H, m), 4.30-4.37 (1H, m), 5.18 (2H, s), 5.92 (1H, s), 6.53-6.65 (2H, m), 6.96 (1H, t, J = 9.0 Hz), 7.06 (2H, d, J = 8.1 Hz), 7.34 (2H, d, J = 8.1 Hz), 7.91 (1H, s).

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-2-fluoro-1-isopropoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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588-63-6, name is (3-Bromopropoxy)benzene, 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. Product Details of 588-63-6

The 148mgNa dissolved in 20ml of absolute ethanol until complete dissolution, 6-(3,5-difluoro)benzyl-2-thiouracil 234mg (0.92mmol) and 1- (3-bromo-propoxy) benzene 297mg (1.38mmol) was added thereto, TLC the reaction was complete after stirring overnight at room temperature; column chromatography, P:E = 5:1,2:1,1:1, the final product was 222mg, as a white solid, a yield of 62.14percent

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University; Zhang, Liang; FU, YUHONG; Qin, Hua; Wang, Xiao Wei; Liu, Jun Yi; (30 pag.)CN103864699; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, belongs to ethers-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 60876-70-2, category: ethers-buliding-blocks

Compound (T-22) (179.7 g, 784.5 mmol), bispinacolato diborane (239.0 g, 941.4 mmol), potassium acetate (92.4 g, 941.4 mmol), bis(diphenylphosphino ferrocene dichloropalladium(II) (10.0 g, 13.7 mmol) and 1,3-dioxane (1,000 mL) were mixed, and the resulting mixture was stirred at 90 C. for 4 hours. The reaction mixture was allowed to cool to room temperature, and then poured into water, and subjected to extraction with heptane (800 mL). The extracted layer was washed with water (1,000 mL) and saturated brine (500 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent:heptane) to obtain compound (T-23) (182 g, 659 mmol, 84.10).

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; JNC Co., Ltd.; JNC Petrochemical Co., Ltd.; Kobayashi, Masahide; Goto, Yasuyuki; Goto, Mayumi; (103 pag.)KR2016/2826; (2016); A;,
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Synthetic Route of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

In a clean dry round bottom flask, l-bromo-3.5-dimethoxybenzene (8.00 g, 36.9 mmol) was added to 300 ml of dry dichloromethane. The solution was cooled down to 0C and BetaIota (25.00 g, 100 mmol) was added dropwise. After 2 hours, the mixture was allowed to warm to room temperature and stirred over night. Methanol (10 ml) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours. Then saturated sodium bicarbonate (100 ml) was added and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine and then dried over Na2S04. The residue, after concentration, was purified using chromatography using ethyl acetate/hexane (1:4 v/v) eluent. Yield = 4.39 g (63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; POLYMEDIX, INC.; UNIVERSITY OF MASSACHUSETTS; LI, Yan; THAKER, Hitesh; TEW, Gregory N.; LIU, Dahui; PAN, Wenxi; WO2013/90185; (2013); A1;,
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