Category: ethers-buliding-blocks

Synthetic Route of 62257-15-2,Some common heterocyclic compound, 62257-15-2, name is 2-Fluoro-5-methoxyaniline, molecular formula is C7H8FNO, 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.

E. Preparation of N-benzyl-2-fluoro-5-methoxyaniline This procedure was patterned after that of Tietze and Grote, Chem Ber. 126(12), 2733 (1993). A solution of 2.73 g of 2-fluoro-5-methoxyaniline and 2.67 g of benzaldehyde in 48 ml of methanol was treated with 3.43 g of zinc chloride and then cooled in an ice bath. Sodium cyanoborohydride (1.58 g) was added in small poroom temperature ions over 30 minutes and the reaction was stirred for five hours at room temperature. After evaporation of the solvent, the residue was slurried in 40 ml of 1 N sodium hydroxide solution and then extracted twice with ether. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was recrystallized from hexane to afford 2.61 g and the mother liquors were chromatographed on silica gel using 20:1 hexane/ether to afford another 1.4 g of the subtitle compound (90%). mp. 56-58C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-methoxyaniline, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; EP950657; (1999); A2;,
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Adding a certain compound to certain chemical reactions, such as: 22483-09-6, name is 2,2-Dimethoxyethanamine, 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 22483-09-6, Safety of 2,2-Dimethoxyethanamine

General procedure: A solution of amino acetaldehyde dimethyl acetal 2a (10. 514 g, 1.081 mL, 10 mmol), purchased from Alfa Aesa, and an aldehyde (10 mmol) in dry ethanol was placed in a round bottom flask and stirred for 12 h. To that solution, sodium borohydride powder (0.567 g, 15 mmol) was added at 0 C slowly over 5 minutes. the solution was then warmed to room temperature. After stirring for 4 h, the reaction was quenched with 3 drops of water and the mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure, the residue was extracted with 100 mL of ethyl ether and washed with100 mL of water. The organic layer was dried over MgSO4 anhydrous. Ethyl ether was then evaporated and the resulted viscous liquid was purified by flash column chromatography (SiO2; 4:1 then 3:1 and finally 1:1hexanes/ethyl acetate).

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Reference:
Article; Luu, Quang H.; Guerra, Jorge D.; Castaneda, Cecilio M.; Martinez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue; Tetrahedron Letters; vol. 57; 21; (2016); p. 2253 – 2256;,
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Application of 33311-29-4, A common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, 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.

tert-Butyl (3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate (800 mg, 2.37 mmoL) and 4-(2-methoxyethoxy)aniline (576 mg, 2.84 mmoL) were suspended in tert-amyl alcohol (14 mL) and acetic acid (5 drops). Heated to reflux for 4 h. After cooling, solvent was removed via rotary evaporation. The dark oil was partitioned between water/brine and THF (10 mL each), agitated, and separated layers and dried organic phase over sodium sulfate. The solvent was removed via rotary evaporation to afford a purple solid, 0.55 g. LC/MS (RT=2.997/(M+1)) 470.2. Additional 150 mg of product minus the (BOC) protecting group crystallized from the aqueous layer

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
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Synthetic Route of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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 1: tert-butyl 1-(2-(trifluoromethoxy)phenyl)piperidin-4-ylcarbamate A mixture of 1-bromo-2-(trifluoromethoxy)benzene (2.40 g, 9.96 mmol), tert-butyl N-(4-piperidyl)carbamate (1.99 g, 9.96 mmol), Pd2(dba)3 (546 mg, 597 umol), BINAP (744 mg, 1.20 mmol), t-BuONa (6.47 g, 69 mmol) in toluene (50 mL) was stirred at 90 C. for 16 h. Cooled to rt, filtered and concentrated, eluted with EtOAc (50 mL), washed with H2O (100 mL), then extracted with EtOAc (100 mL*3), washed with brine (50 mL*2), dried, concentrated to afford methyl 5-formyl-2,4-dimethylbenzoate (1.6 g, 32.6%) as brown gum. ESI-MS (EI+, m/z): 361 [M+H]+.

The synthetic route of 64115-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
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Some common heterocyclic compound, 352-67-0, name is 1-Fluoro-4-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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: C7H4F4O

EXAMPLE 49 3-Trifluoromethoxy-10-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine; a) 2-Fluoro-5-trifluoromethoxy-benzaldehyde; A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 ml) was cooled to <-70 C. Tert.-butyllithium (86 ml of a 1.5 molar solution in pentane, 129 mmol) was added at such a rate that temperature was kept <-70 C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 ml, 150 mmol) was added dropwise keeping temperature <-70 C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with ether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 80:2). The title compound (11.0 g, 53%) was obtained as a light yellow oil. 1H-NMR (300 MHz, DMSO): delta=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 352-67-0, its application will become more common. Reference:
Patent; Buettelmann, Bernd; Knust, Henner; Thomas, Andrew William; US2006/128691; (2006); A1;,
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Application of 363-47-3, A common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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 solution of 3,5-difluoro-4-methoxyaniline (100 mg, 0.628 mmol) and triethylamine (131 mul, 0.943 mmol) in DCM was coiled and added 2-chloroacetyl chloride (60.0 mul, 0.754 mmol). The reaction mixture was stirred at room temperature for 2 h. Reaction was diluted with DCM, washed with 0.5 M HCl, water, brine, dried over Na2SO4 and evaporated. The crude brown solid, 2-chloro-N-(3,5-difluoro-4-methoxyphenyl)acetamide (120 mg, 0.509 mmol, 81% yield) was used for the next step without purification. 1H-NMR (400 MHz, CDCl3) delta ppm 8.15 (s, 1H), 7.21 (d, 1H, J=8 Hz), 4.18 (s, 1H), 3.97 (s, 3H); ESI-MS: m/z 235.82 (M+H)+.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); A1;,
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These common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, 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. name: (4-Phenoxyphenyl)methanamine

General procedure: One equivalent of intermediate 14a or 14b was dissolved in THF and 1.5 eq of the proper amine, 1.5 eq of TEA, 1.5 eq of NaI and 0.3 eq of (CH3COO)2Pd were added to this solution. The reaction was conducted under muW, at 100C, for 20min. The resulting mixture was filtered through Celite, dried in vacuo and reconstituted in DCM. The organic phase was washed with water (3×50mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by column chromatography using DCM/MeOH (9:1 v/v) as mobile phase giving derivative 15 in 38% yield and intermediates 16a-i in 55-75% yield.

The synthetic route of (4-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Musella, Simona; di Sarno, Veronica; Ciaglia, Tania; Sala, Marina; Spensiero, Antonia; Scala, Maria Carmina; Ostacolo, Carmine; Andrei, Graciela; Balzarini, Jan; Snoeck, Robert; Novellino, Ettore; Campiglia, Pietro; Bertamino, Alessia; Gomez-Monterrey, Isabel M.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 773 – 781;,
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These common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, 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. Recommanded Product: 2-Methoxyethylamine

A solution of 6-amino-4-fluoronicotinonitrile (obtained in step 9, 1 .10 g, 8.02 mmol) in DMA (20 mL) was treated with 2-methoxyethylamine (2.07 mL, 24.1 mmol) and DIPEA (4.20 mL, 24.1 mmol), heated to 50 C and stirred for 15 h. The reaction mixture was cooled to room temperature and concentrated. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100). The product containing fractions were concentrated and dried under vacuum to give the title compound as an off-white solid

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

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOEPFEL, Thomas; LEBLANC, Catherine; MAH, Robert; MALLET, Franck; MARTZ, Julie; LIAO, Lv; XIONG, Jing; HAN, Bo; WANG, Can; ZHAO, Xianglin; (56 pag.)WO2016/151500; (2016); 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., SDS of cas: 321-28-8

EXAMPLE 1 Preparation of 1-(3-Fluoro-4-Methoxy-Phenyl)-Hexan-1-One; 2-Fluoroanisole (3.15 g, 25.0 mmol) is dissolved in dry dichloromethane (25 mL). While stirring the resulting solution under nitrogen, aluminum chloride is added (3.92 g, 29.4 mmol). This solution is cooled with a cold water bath and hexanoyl chloride (3.87 g, 28.8 mmol) is added drop wise such that the internal temperature is maintained at or below 20 C. Upon complete of addition, the reaction is stirred 30 minutes at room temperature. The dark orange solution is cooled to -10 C. and slowly quenched by the addition of water (25.0 mL) while keeping the internal temperature below 0 C. The mixture is transferred to a separatory funnel, the organic layer (bottom) is collected and the aqueous discarded. The organic solution is then washed with 5N NaOH (12.5 mL) and again with water (12.5 mL). The crude organic is concentrated by vacuum distillation and diluted with heptane to a final volume of about 20 mL. The slurry is heated until all solids are dissolved and allowed to cool to room temperature. The product crystallizes upon cooling. The slurry is further cooled to 0 to 5 C. for one hour and filtered. The wet cake is washed with cold (0 C.) heptane (2×2.5 mL) and the product dried under vacuum.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huffman, Mark A.; Qin, Xue-Zhi; Rosen, Jonathan D.; US2006/247319; (2006); A1;,
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Application of 157869-15-3, 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. 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

1 k (0.3 mmol, 67 mg), [RhCp*Cl2] 2 (0.015 mmol, 9.3 mg) and hexafluoroisopropanol (2 mL) were sequentially added to a 15 mL reaction tube.The reaction tube was sealed in an air atmosphere, and the reaction was stirred at 120 C for 20 h. After the completion of the reaction, the reaction tube was cooled to room temperature, and 10 mL of water was added thereto, followed by extraction with ethyl acetate (10 mL × 3), and the organic phase was washed successively with water and brine, and dried over anhydrous sodium sulfate. filter,Spin dry, separated by silica gel column (petroleum ether / ethyl acetate = 5 / 1)The white solid product 2k (35 mg, 72%).

The chemical industry reduces the impact on the environment during synthesis 2-((4-Methoxyphenyl)ethynyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Henan Normal University; Fan Xuesen; Jia Ruixue; Zhang Xinying; Li Bin; (18 pag.)CN110183443; (2019); A;,
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