Tag: M.W=200-300

Application of 450-88-4,Some common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Description 18; : 3-Bromo-6-fluoro-2-(methyloxy)benzaldehyde (D18)To a solution of diisopropylamine (6.89 g, 9.6 ml_, 68.3 mmol) in THF (100 ml.) at -78 C was added n-butyl lithium (33.5 ml. of 1.6 M solution in hexane, 53.6 mmol) over 3 mins. After stirring at -78 C for 10 mins, 2-bromo-5-fluroanisole (10 g, 48.8 mmol) in THF (20 ml.) was added dropwise over 15 mins. After completion of the addition, the mixture was stirred at -78 C for 1 hr and then DMF (3.91 g, 4.12 ml_, 53.6 mmol) was added dropwise over 3 mins and stirring was continued at -78 C for 45 mins. Saturated NH4CI solution was added and the mixture allowed to each room temperature. Diethyl ether and 2M HCI were added, the product was extracted into diethyl ether and the combined extracts were washed with brine, dried and evaporated. Chromatography on silica gel followed by trituration of the product with diethyl ether gave the title compound (D18) as a yellow solid (6.84 g) NMR (deltaH), (CDCI3): 3.97 (3H, s), 6.90 (1 H, m), 7.76 (1 H, dd, J = 5.9, 11.0 Hz), 10.34 (1 H, s).

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-4-fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
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Some common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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. SDS of cas: 262587-05-3

General procedure: To a mixture of l-bromo-3-(difluoromethoxy) benzene (1 g, 4.5 mmol), bis(tri-tert- butylphosphine) palladium(O) (460 mg, 0.9 mmol) in 1,4-dioxane (30 ml) under argon atmosphere was added 0.5 M of 2-tert-butoxy-2-oxoethyl zinc chloride in ether (22.5 ml). The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between saturated NH4C1 and EtOAc. The organic extract was washed with brine, dried over sodium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography eluting with 0-10% EtOAc in Hexane to afford 1119.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 262587-05-3, its application will become more common.

Reference:
Patent; CALITHERA BIOSCIENCES INC.; LI, Jim; CHEN, Lijing; GOYAL, Bindu; LAIDIG, Guy; STANTON, Timothy, Friend; SJOGREN, Eric, Brian; WO2013/78123; (2013); A1;,
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These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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. COA of Formula: C5H10Br2O2

Reference Example 2; Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylateTo DMF solution (1.8 L) comprising diisopropyl malonate (1437 g), sodium hydride (367 g) was added at 15 C. Subsequently, 1,3-dibromoacetone dimethylacetal obtained from Reference example 1 was added thereto, stirred at 130 C. for 24 hours, followed by further stirring for three days. Upon the completion of stirring, the reaction was terminated by adding aqueous solution of ammonium chloride, and extraction was carried out using hexane. The organic layer was washed with water, and then dried over magnesium sulfate. Solids were removed, and the filtrate was dried under reduced pressure. Thus obtained residues were subjected to flash column chromatography (using 10:1 (v/v) hexane/ethyl acetate as an eluent) to obtain the title compound (1.5 kg).1H-NMR (CDCl3): 5.08 (2H, m), 3.15 (6H, s), 2.69 (4H, s), 1.24 (12H, m).

The synthetic route of 1,3-Dibromo-2,2-dimethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/298894; (2009); 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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

4-BenzyloxyanilineHCl (86.1 mmol, 20.3 g), diethylbromomalonate (86. 1mmol, 14.7 ml) and N, N-diisopropylethylamine (86.1 mmol, 15 ml) in toluene (200 ml) was heated at 100C for 36 hours. The reaction mixture was concentrated, dissolved in water (500 ml) and extracted with EtOAc (3 X 300 ml). The organic phase was dried over Na2S04, concentrated and purified by flash chromatography (Si02, 50% EtOAc/hexanes) to provide compound 4A as a brown solid (13.7 g, 45%)

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; BRISTOL-MYERS SQUIBB COMPANY; WO2003/91252; (2003); 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. 170015-99-3, name is 2-(4-(Trifluoromethoxy)phenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H10F3NO

Preparation of Intermediate Ethyl 4-(trifluoromethoxy)phenethylcarbamate (I-51c) Using an analogous procedure and workup as described for the preparation of intermediate I-1c above, 2-(4-(trifluoromethoxy)phenyl)ethanamine (I-51b: 3.1 g, 15.1219 mmol) in chloroform (31 mL) was reacted with chloro ethyl formate (1.72 mL, 18.146 mmol) and 2N Na2CO3 solution (31 mL) at 0 C. The resulting mixture was stirred at room temperature for 3 hours to afford the crude product. Purification by column chromatography on silica gel (10% ethylacetate in hexane) afforded 3.2 g of the product (76% yield). 1H NMR (300 MHz, CDCl3): delta 7.30-7.10 (m, 4H), 4.75-4.65 (m, 1H), 4.15-4.05 (m, 2H), 3.4 (q, 2H), 2.8 (t, 2H), 1.3-1.2 (m, 3H). LCMS: 70.91%, m/z=278.1 (M+1)

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 170015-99-3.

Reference:
Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of ((2-Bromoethoxy)methyl)benzene

In a round bottom flask aniline (2.0 g, 21.5 mmol, 2.0 mL), 2,6-lutidine (2.30 g, 21.5 mmol) and benzyl 2-bromoethyl ether (4.6 g, 21.5 mmol, 3.4 mL) were combined in DMF (10 mL) and stirred at 100° C. overnight. The reaction was allowed to cool and then diluted with ethyl acetate (50 mL). This was washed with water (3*20 mL) and the organics were dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (0-50percent B, 100 g, 19.5 CV, 85 mL/min) to afford 2.22 g (37percent) of (2-benzyloxy-ethyl)-phenyl-amine (21) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3) deltaC 43.6, 68.6, 73.2, 113.1, 117.5, 127.5, 127.7, 128.4, 129.1, 138.2, 148.1.

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; GE Healthcare Limited; Jones, Paul Alexander; US9168317; (2015); B2;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-4-fluoro-2-methoxybenzene

To tert-butyl (R)-3-methylpiperazine-1 -carboxylate (5.37 g, 26.8 mmol) and 1 – bromo-4-fluoro-2-methoxybenzene (5.00 g, 24.4 mmol) in toluene (50 ml.) was added sodium tert-butoxide (4.69 g, 48.8 mmol) followed by BrettPhos palladacycle G3 (66.4 mg, 0.0732 mmol). The mixture was sealed under nitrogen and stirred at 100 C and after 1 h the mixture was cooled to ambient temp, diluted with ethyl acetate and water. The organic layer was dried with sodium sulfate, filtered, and concentrated. Crude product was purified by column chromatography (0-40%, ethyl acetate/hexanes) to provide the product. MS(EI) for C; /H:FN;.C. found 325 [M+H]+.

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 450-88-4.

Reference:
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
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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 36805-97-7 as follows. Formula: C11H25NO2

3-Hydroxy Phenyl Acetic Acid-t-butyl Ester (Reagent F) A stirred suspension of 3-hydroxy-phenyl acetic acid (1.52 g, 10 mmol) in anhydrous toluene (20 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (9.6 mL, 40 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. Th residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (1.17 g, 56%). 1H-NMR (300 MHz, CDCl3):delta 1.47(s, 9H), 3.49(s, 2H), 6.30(s, 1H), 6.70-6.79 (m, 2H), 6.81(d, J=7.6 Hz, 1H), 7.16(t, J=7.7 Hz, 1H).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US6252090; (2001); B1;,
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Electric Literature of 5111-65-9, These common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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.

6-Methoxy-2-bromonaphthalene (0.97 g, 4.1 mmol) was dissolved in 20 mL of dry THF, protected under nitrogen, (3.4 mL, 8.2 mmol) was added, stirred for 1 hour, and then anhydrous DMF (0.941 mL, 12.3 mmol) was added dropwise at -78 C,The reaction was continued at 78 C for 1 hour, rose to room temperature, acidified to pH = 5 with 2N hydrochloric acid, extracted with ethyl acetate, washed with water, saturated brine Washed with anhydrous sodium sulfate, filtered and concentrated, n-hexane / ethyl acetate (15: 1) column chromatography to isolate 6-methoxy-2-naphthyl Aldehyde, the yield of 88.6%.

Statistics shows that 2-Bromo-6-methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 5111-65-9.

Reference:
Patent; Liaocheng University; Liu Guoyun; Yang Jie; Li Xiaoteng; Guo Shangjing; (19 pag.)CN105111054; (2017); B;,
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Application of 24878-25-9, 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. 24878-25-9 name is 2,2′-Oxydianiline, 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.

General method: An equimolar mixture of RhCl3·3H2O with the corresponding ligand Ln in 15mL of hot methanol was refluxed for 24h. After cooling to room temperature, the solid formed was filtered off and dried in vacuum; then it was washed with cold methanol (2×4mL). Synthesis of [RhIII(L1)Cl3] (1) RhCl3 3H2O (0.080g, 0.304mmol), L1 (0.050g, 0.231mmol). Yellow solid. Yield 68% (0.085g). M. p.: above 250 C. Anal. Calc. for C12H12Cl3N2ORh (1): C, 35.20; H, 2.95; N, 6.84. Found; C, 34.95; H, 2.87; N, 6.80%. IR data (KBr, cm-1): 3433 (NH); 3200, 3096 (CHaromatics); 1602, 1491 (C=C); 1264 (C-O-C). Raman data (cm-1): 414 (Rh-N); 316 (Rh-Cl); 279 (Rh-O). 1H NMR (DMSO-d6) delta=7.53 (d, 2H, NHA, 2J=9.97Hz), 7.50 (d, 2H, H3, 3J=7.26Hz), 7.24 (d, 2H, NHB, 2J=9.97Hz), 7.20-7.12 (m, 4H, H4, H6), 7.03 (dd, 2H, H5, 3J=7.03, 3J=7.03Hz).

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

Reference:
Article; Alvarado-Rodriguez, Jose G.; Hernandez-Balderas, Uvaldo; Andrade-Lopez, Noemi; Salazar, Veronica; Sanchez-Cabrera, Gloria; Zuno-Cruz, Francisco J.; Polyhedron; vol. 117; (2016); p. 453 – 462;,
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