Tag: M.W=200-300

Synthetic Route of 873980-68-8, These common heterocyclic compound, 873980-68-8, name is 4-Bromo-2-methoxy-5-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.

Step 2: BBr3 (1 M solution in CH2CI2, 138 mL, 138 mmol) was added to a solution of the intermediate of step 1(12.0 g, 55.6 mmol) in CH2CI2 at OC and the mixture was stirred rt for 10 h. Aq. NaHCO3 was added and the mixture was extracted with CH2CI2. The combined organic layers were washed with water, brine, were dried the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiC2, Cy/EtOAc) to yield the desired compound (10 g, 89%).

The synthetic route of 873980-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (2015); A1;,
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Application of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 346: Ethyl (2E)-3-{1-[4-(difluoromethoxy)phenyl]-3-(2-phenylethyl)-1H-indol-5-yl}propenoate; To a solution of the compound obtained at Example 141 (200 mg) in n-butyl acetate (15 ml) were added 1-bromo-4-(difluoromethoxy)benzene (281 mg), palladium acetate (28 mg), 2-(di-tert-butylphosphino)biphenyl (75 mg) and tripotassium phosphate (535 mg), and the mixture was heated and stirred at 120C for 12 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:11) to afford the above-identified compound (227 mg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(difluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP2141148; (2010); A1;,
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Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (i .29 g,52.8 mmol) in dry THF (50 mL). The mixture was ref luxed and about 5% of a solution of 3-bromophenol (i3.9 g, 52.8 mmol) was added. When the reaction had started, the solution of the bromide was added drop-wise and the mixture was then ref luxed for one more hour. Themixture was cooled down to about 5 00 and a solution of the cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added drop-wise. The mixture was stirred at rt for 72 h, then the reactio was quenched with cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc),which gave the title compound (8.5 g, 54%).

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

Reference:
Patent; MEDIVIR AB; KALAYANOV, Genadiy; TORSSELL, Staffan; WAeHLING, Horst; WO2015/34420; (2015); A1;,
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Reference of 204452-91-5, A common heterocyclic compound, 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, molecular formula is C11H16N2O2, 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.

Step 3: Preparation of 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine NBS (38.3 g, 215 mmol) was added in batches to a solution of 7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (42.7 g, 205 mmol) in MeCN (1 L) at room temperature. The reaction solution stirred for 1 hour and concentrated. The resulting residue was dissolved in CH2Cl2, washed with 1 M NaOH aqueous solution and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was subjected to column chromatography to obtain the title compound 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (47.5 g, total yield of three steps: 81%). 1H NMR (400 MHz, CDCl3): delta 7.27 (s, 1H), 5.55 (s, 1H), 5.39 (br s, 1H), 3.45 (s, 6H), 3.38 (m, 2H), 2.70 (t, J = 6.0 Hz, 2H), 1.88 (m, 2H); MS m/z (ESI): 287.0 [M+H]+.

The synthetic route of 204452-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Shanghai Hansoh Biomedical Co., Ltd.; GAO, Peng; XIU, Wenhua; WANG, Shaobao; LIU, Lei; BAO, Rudi; (94 pag.)EP3444250; (2019); A1;,
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Synthetic Route of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

a) 6-Bromo-3-(3-phenoxy-propoxy)-pyridine-2-carboxylic acid methyl esterA mixture of -bromo-3-hydroxypicolinic acid methyl ester (lOOmg, 0.43 mmol), sodium hydride (60percent dispersion in mineral oil) (17.3mg, 0.43 mmol), 3-phenoxypropyl bromide(68 muL, 0.43 mmol), in dimethyl acetamide (1.5 mL) was heated at 9O0C for 3 hours. The reaction was allowed to cool, poured onto water and then extracted with ethyl acetate (2 x3mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by silica chromatography eluting with 100percent petroleum ether to 30percent ethyl acetate/petroleum ether to obtain a white solid (95mg, 60percent). 1H NMR (300 MHz,CDCl3) delta: 7.48 (IH, d), 7.24-7.21 (3H, m), 6.91-6.86 (3H, m), 4.19 (2H, t), 4.15 (2H, t),3.88 (3H, s), 2.30-2.22 (2H, m).

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

Reference:
Patent; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; WO2009/39553; (2009); 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. 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

General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether-ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC-MS analysis). The purity of the recovered MeOH was measured as more than 99 % by GC, and the water content of the recovered MeOH was measured as less than 0.12 % by use of the Karl Fischer method.

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:
Article; Guo, Ying; Ji, Si-Zhe; Chen, Cheng; Liu, Hong-Wei; Zhao, Jian-Hong; Zheng, Yu-Lin; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 41; 11; (2015); p. 8651 – 8664;,
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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. 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H10F3NO

To a solution of 4-(4-(trifluoromethyl)phenoxy)aniline (AK Scientific, 63 mg, 0.25 mmol) in DCM 2-chloroacetyl chloride (Sigma, 34 mg, 0.30 mmol) and triethylamine (Sigma, 30.4 mg, 0.30 mmol) were added and the reaction stirred overnight. Upon reaction completion the crude was purified by silica gel chromatography (10-40% EtOAc/hexanes) to yield 65 mg (78%).1H NMR (400 MHz, CDCl3): d 8.25 (s, 1H), 7.63- 7.51 (m, 4H), 7.12- 6.99 (m, 4H), 4.22 (s, 2H). HRMS: (-ESI): calcd. for: C15H10O2NF3Cl = 328.0358, found: 327.0356

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; NOVARTIS AG; SPRADLIN, Jessica; WARD, Carl, C.; NOMURA, Daniel, K.; SCHIRLE, Markus; TALLARICO, John, A.; MCKENNA, Jeffrey; MAIMONE, Thomas, John; HU, Xirui; (472 pag.)WO2020/76996; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, 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 103291-07-2, 103291-07-2

To a solution of 69A (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 69B (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3 H) 7.03-7.45 (m, 3 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, 4-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
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Adding some certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 19056-40-7. 19056-40-7

Method 12 2-[(4-Bromo-3-methoxyphenyl)diazenyl]-2-cyanoacetamide. Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice- cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml x 3), and dried to yield the title compound as a yellow solid (34.4 g, 94 percent). 1H NMR: 11.70 (s, 1 H), 7.90 (s, 1 H), 7.50 (m, 2 H), 7.35 (s, 1 H), 7.20 (d, 1 H), 3.90 (s, 3 H); m/z: 296.

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 4-Bromo-3-methoxyaniline.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/90353; (2008); 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H8BrFO

Step 1. 5-[2-(4-fluoro-phenoxy)-ethoxy]-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one A mixture of 2-hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-one (21.7 g; J. Org. Chem 1982, 47, 4329), K2CO3 (17.7 g) and 1-(2-Bromo-ethoxy)-4-fluoro-benzene (40.3 g) in DMF (400 ml) were stirred for 72 hours at 120 C. The reaction was then cooled to room temperature and the solvent removed in vacuo. The residue was then washed with saturated NaHCO3 solution and the organics extracted with EtOAc (3*200 ml). The organics were then combined, dried (MgSO4) and the solvent removed in vacuo yielding a dark brown oil which was purified by flash chromatography on silica eluding 20% EtOAc in isohexane giving the title alkylated ketone (15.97 g, 44%). MS (ES+) 341 [M+H]+.

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; Belanger, Patrice Charles; Collins, Ian James; Hannam, Joanne Claire; Harrison, Timothy; Lewis, Stephen John; Madin, Andrew; McIver, Edward Giles; Nadin, Alan John; Neduvelil, Joseph George; Shearman, Mark Steven; Smith, Adrian Leonard; Sparey, Timothy Jason; Stevenson, Graeme Irvine; Teall, Martin Richard; US2004/29862; (2004); A1;,
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