Category: ethers-buliding-blocks

Adding some certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8. 22236-10-8

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l).

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-(Difluoromethoxy)aniline.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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 75148-49-1, 75148-49-1

To a solution of 3-bromobenzylaldehyde diethyl acetal (0.518 g, 2.0 mmol) and15 anhydrous toluene (4 ml) was added 1-methylpiperazine (0.240 g, 2.4 mmol) followedby Pd2(dba)3 (0.018 g, 0.02 mmol), racemic BINAP (0.037 g, 0.06 mmol) and Na01Bu(0.326 g, 3.4 mmol). The reaction mixture was placed into an oil bath preheated to 100C and stirred at this temperature for 18 h under argon, then allowed to cool to roomtemperature. Aqueous HCI (1M; 10 ml) was added, the mixture was vigorously stirred20 for 2.5 h, then the pH adjusted to 13 with 6M aqueous NaOH and extracted with ethylacetate (3 x 30 ml). The combined organics were dried (Na2S04), concentrated in vacuoand the residue was absorbed on silica gel and placed on a 10 g isolute column. Elutionwith ethyl acetate I dichloromethane (v/v; 4:1) and then a gradient of methanol (3 to 7%)in ethyl acetate afforded the title compound as a yellow oil (0.170 g, 42%). 1 H-NMR (50025 MHz, DMSO-d6) 2.22 (s, 3H, N-Me), 2.46 (t, J = 5.0 Hz, 4H, piperazine C-H), 3.21 (t, J =5.1 Hz, 4H, piperazine C-H), 7.28 (m, 2H, PhH), 7.41 (m, 2H, PhH), 9.94 (s, 1 H, CHO);[00122] LC- MS (ESI, m/z): Rt = 0.86 min- 205 (M+Ht.

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, 3-Bromobenzaldehyde Diethyl Acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22236-10-8

1-[(6-AMINOPYRIDIN-3-YL) METHYL]-3-{[4-(DIFLUOROMETHOXY) phenyl] AMINO} ? 4-PHENYL- 1H-PYRROLE-2, 5-dione A mixture OF TERT-BUTYL {5- [ (3-CHLORO-2, 5-dioxo-4-phenyl-2, 5-dihydro-1H-pyrrol-1- yl) methyl] PYRIDIN-2-YL} CARBAMATE (0.70 g, 1.7 mmol) and 4- (difluoromethoxy) aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150C for 8 min.. The solvent was evaporated and the residue was purified on a pre-packed SIO2COLUMN (ISOLUTE0 SI, lOg/70 mL) using CH2C12 and then CH30HL CH2CL2 (1: 99,2 : 98 and then 5: 95) as eluant to give 0.4 g (54%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) 8 7.99 (bs, 1H), 7.67-7. 62 (m, 2H), 7.14-7. 04 (m, 3H), 6.91 (d, J =8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H) and 4.60 (s, 2H).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/5416; (2005); A1;,
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2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, 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. 2930-05-4

General procedure: A 50mL sealed tube with a magnetic stirring bar was evacuated and backfilled will CO2 for three times, potassium organoaluminate (0.1mmol), (n-Bu)4NI (0.05mmol), epoxide (2.0mmol), and 1.0mL THF were added. The reaction mixture was stirred at 50C (heating mantle temperature) for 24h. The reaction was then quenched with H2O (10mL) and extracted with ethyl acetate (3¡Á15mL). The combined organic layers were dried over Na2SO4 and concentrated. The yields were determined by 1H NMR spectroscopy with trichloroethylene (90muL, 1mmol) as an internal standard. Then, the reaction mixture was purified on silica gel column chromatography (petroleum ether/EtOAc: 3/1). All cyclic carbonates were identified through comparisons with the corresponding 1H NMR, 13C NMR data reported in the literatures [7].

Statistics shows that 2930-05-4 is playing an increasingly important role. we look forward to future research findings about 2-((Benzyloxy)methyl)oxirane.

Reference:
Article; Guo, Zhiqiang; Yan, Leilei; Liu, Yaoming; Wu, Xiaoqin; Wei, Xuehong; Journal of Organometallic Chemistry; vol. 922; (2020);,
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Adding some certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5. 1535-73-5

General procedure: To a stirred solution of 11 (13.14 mmol) in 1,2-dichloroethane (240 mL) were added appropriate substituted anilines (19.71 mmol) and AcOH (13.14 mmol), and the mixture was heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture was cooled to 0 ¡ãC, and MeOH (60 mL) and THF (20 mL) were added. To it, (AcO)3BHNa (26.20 mmol) or NaBH4 (52.56 mmol) was added portionwise, and then the reaction mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7?8 at 0 ¡ãC with 1 NHCl, and then the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2¡Á 300 mL). The combined organic layers was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel to afford the titled compounds as a solid.

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 3-Trifluoromethoxyaniline.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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The chemical industry reduces the impact on the environment during synthesis 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, I believe this compound will play a more active role in future production and life. 54149-17-6

Example 35 Preparation of N-{2-[2-(2-methoxyethoxy)ethoxy]phenyl}-17-methylmorphinan-3-amine (35), hydrochloride salt (35) Step 1. Synthesis of l-bromo-2-(2-(2-methoxyethoxy)ethoxy)benzene, A mixture of 2-bromophenol (0.448g, 2.59 mmol), l-bromo-2-(2- methoxyethoxy)ethane (0.383mL, 2.85 mmol), and potassium carbonate (1.073g, 7.76 mmol) in dimethyl formamide (5 mL) was stirred at 60 C overnight. The reaction mixture was poured into 20 mL of 5% LiCl solution and extracted with ethyl acetate 3x30mL. The organic layer was washed with brine, was dried over sodium sulfate, was filtered and was concentrated. After drying under high vacuum, the pure product was obtained as colorless oil (656.7 mg) in 92% yield. *Eta NMR (400 MHz, CDCl-3): delta 7.54 (d, 1H), 7.24 (t, 1H), 6.92 (d, 1H), 6.83 (t, 1H), 4.40 (t, 2 H), 3.92 (t, 2H), 3.80 (t, 2H), 3.58 (t, 2H), 3.39 (s, 3H). MS (EI) for CnHi5Br03: 292 (MNH4+).

The chemical industry reduces the impact on the environment during synthesis 54149-17-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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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. 5905-69-1

A stirred mixture of l-bromo-4-(difluoromethoxy)benzene (0.54 mL, 4 mmol), bis(pinacolato)diboron (1.21 g, 4.8 mmol), l, -bis(diphenylphosphino)ferrocene- palladium dichloride (0.32 g, 0.4 mmol), and potassium acetate (1.18 g, 12 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC- MS and TLC. After 21 h, the reactions were cooled to rt then filtered through celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2- (4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane. 1H NMR (400 MHz, DMSO-de) delta ppm 7.76 (2 H, m), 7.30 (3 H, m), 1.29 (12 H, s).N-(5-(4-(Difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3- methyl-2-(pyridin-2-yl)quinolin-4-amine.

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; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
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366-99-4, 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. 366-99-4 name is 3-Fluoro-4-methoxyaniline, 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.

Example 18 Synthesis of (4-Chloro-6-cyclohexylmethoxy-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl)-amine (114) To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by addition of NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexanes:ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp 98¡ã C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.36; MS (ESI): m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7). Example 19 Synthesis of 6-Cyclohexylmethoxy-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4-diamine (115) [0741] Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70:30 hexanes:ethyl acetate), mp 181¡ã C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.17; MS (ESI): m/z 472 (M+H, 100), 261 (1.5).

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; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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1535-73-5, 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. 1535-73-5, name is 3-Trifluoromethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 (4-TERT-BUTYL-PHENYL)- {4- [2- (4-TRIFLUOROMETHYL-PIPERIDIN-1-YL)-PYRIMIDIN-4-YL]-ISOQUINOLIN- 1-YL}-AMINE To a solution of (4-TERT-BUTYLPHENYL)- [4- (2-CHLOROPYRIMIDIN-4-YL)-ISOQUINOLIN-1-YL] AMINE (0.07 g, 1.80 x 104 m) in n-butanol (30 mL) is added 4-trifluoromethylpiperdine (0.07 g, 4. 57 x 104 m) and triethylamine (0. 50 mL). The mixture is heated to 100¡ãC for 16 hours and then allowed to cool to room temperature. The mixture is concentrated in vacuo and then dissolved in methylene chloride (75 mL). The organic phase is washed with a saturated solution of sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to a oil. The oil is purified by flash chromatography (SIO2 : 75percent hexanes/25percent ethyl acetate). A light yellow oil is collected and crystallized from ether, m. p. 179-180¡ãC. CHN analysis calc. percent C: 68.89 ; percent H: 5.98 ; percent N: 13.85. Found percent C: 68.91 ; percent H: 5.73 ; percent N: 13.73.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)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 1515-81-7, 1515-81-7

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), the ketone (1.0 mmol), 2,6-lutidine (164 mL, 151 mg, 1.40 mmol) and TMSOTf (271 muL, 333 mg, 1.50mmol). The mixture was cooled to 0 Cand p-methoxybenzyl methyl ether (167mL, 167 mg, 1.10 mmol) was added. The reaction mixture was allowed to warmslowly to ambient temperature and stirred for 16 h, then it was passed througha column of silica (2 cm x 1 cm) with Et2O. The solvent was removedin vacuo and the residue was purified by column chromatography (0-5%EtOAc/hexanes).

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, 1-Methoxy-4-(methoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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