Category: ethers-buliding-blocks

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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H8FNO

Step C: 2,5-Difluoro-lambda/-{3-[(2-{[3-fluoro-4-(methyloxy)phenyl]amino}-4- pyrimidinyl)acetyl]phenyl}benzamide; To a solution containing 2.4 g (6.2 mmol) of lambda/-{3-[(2-chloro-4- pyrimidinyl)acetyl]phenyl}-2,5-difluorobenzamide and 60 mL of i-PrOH was added 0.92 g (6.5 mmol) of 3-fluoro-4-(methyloxy)phenyl amine and 0.1 mL of cone HCI. The reaction mixture was heated at 80 0C for 20 min, then diluted with an additional 60 mL of i-PrOH and heated at 90 0C for 13 h. The reaction mixture was allowed to cool to rt, then filtered. The filter cake was collected, slurried in DCM, and neutralized by the addition of aqueous NaHCO3. The organic layer was separated and the aqueous layer was further extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated under recduced pressure. The residue was subjected to silica gel chromatography to give 1.76 g (59percent) of the title compound of Step C as a yellow solid: 1H-NMR (d6-DMSO, 400 MHz) delta 10.64 (s, 1 H), 9.83 (s, 1 H), 8.31 (d, 1 H1 J = 5.3 Hz), 8.25 (s, 1 H), 7.77 (d, 1 H1 J = 8.4 Hz), 7.65-7.69 (m, 1 H), 7.61 (d, 1 H1 J = 7.7 Hz), 7.53-7.59 (m, 1 H)1 7.42-7.47 (m, 4 H), 7.27 (d, 1 H, J = 9.2 Hz)1 7.13 (dd, 1 H1 J = 9.5 Hz and 9.5 Hz), 6.64 (d, 1 H, J = 5.3 Hz), 6.20 (s, 1), and 3.80 (s, 3 H), ; ESIMS: 561.07 (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 366-99-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/76140; (2009); 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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-6-methoxynaphthalene

Step 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

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 5111-65-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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. Formula: C11H15BrO2

Step 1: Preparation of 3-(3-aminooxetan-3-yl)benzaldehyde Hydrochloride 3-Bromobenzaldehyde diethyl acetal (11.65 g, 45 mmol) in dry THF (100 mL) at -78 C. was added n-butyl lithium (2.5 M in hexanes, 19 mL, 47 mmol) dropwise. The sample was stirred at -78 C. for ten minutes then added 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfonamide (7.5 g, 43 mmol) dropwise. The sample was stirred at -78 C. for one hour. The mixture was diluted with 200 mL saturated ammonium chloride solution and 200 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate (250 mL). The reaction mixture was cooled to 0 C. was added 1M hydrochloric acid in ethyl acetate dropwise (24 mL, 24 mmol). The reaction mixture was stirred at 0 C. for one hour then vacuum filtered to give the desired product as a slightly off white solid (1.97 g, 9.2 mmol). 1H NMR (400 MHz, DMSO-d6) delta 10.08 (s, 1H), 9.18 (s, 3H), 8.09 (s, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.79-7.73 (m, 1H), 5.03-4.91 (m, 4H).

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

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 41789-95-1

General procedure: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

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; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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Application of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, 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.

To a mixture of 4-fluoro-2-methoxyaniline (25.0 g, 177 mmol), K2C03 (36.7 g, 266 mmol) and Nal (10.6 g, 0.07 mmol) in /- PrOH (250 ml.) was added bis(2-chloroethyl)amine hydrochloride (47 g, 177 mmol). The reaction mixture was refluxed overnight. The solvent was removed and the residue was purified by column chromatography (petroleum ether/EtOAc = 10:1 ) to provide 1 -(4-fluoro-2-methoxyphenyl)piperazine. MS: m/z 212.36 [M+H] +.

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
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Reference of 710-18-9, 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 710-18-9 as follows.

General procedure: Lewis acid (1.0-1.5eq) (powdered AlCl3, powdered FeCl3, 1 or 2 M solution of TiCl4 in CH2Cl2) was added portionwise to a stirred 1 M solution of the aromatic compound in dry CH2Cl2, and then 2a-f (1.2-1.5 eq) was added dropwise at 0C over a period of 2-10 min. The mixture was stirred for several hours at room temperature. Following complete conversion of starting material, as confirmed by GC analysis, the mixture was quenched with H2O and extracted with CH2Cl2 or EtOAc. The combined organic layers were successively washed with satd. aq. NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by distillation or column chromatography on silica-gel, if necessary.

According to the analysis of related databases, 710-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Warashina, Takuya; Matsuura, Daisuke; Kimura, Yoshikazu; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 587 – 593;,
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Application of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

Intermediate 73: (6-BROMO-PYRIDIN-3-YLMETHYL)- (2-PHENOXV-ETHYL)-AMINE A solution of 2-bromo-pyridine-5-carbaldehyde (500MG, 2. 69MMOL) and 2- (PHENOXY)- ethylamine (594mg, 4.3mmol) in anhydrous ethanol (14ML) was stirred at room temperature for 7 hours. Sodium borohydride (102mg, 2. 7MMOL) was then added to the solution, and the resultant mixture was allowed to stir for a further 3 hours before being quenched with water. The resultant mixture was concentrated, to provide (6-BROMO- pyridin-3-ylmethyl)- (2-phenoxv-ethvl)-amine (quantitative), which was’used without further purification. LCMS (Method B): RT = 1. 79 minutes; 307 309 (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; ARGENTA DISCOVERY LIMITED; WO2005/14588; (2005); A1;,
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Application of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-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.

A solution of sodium nitrite (36 g, 0.51 mole) in water (50 mL) was slowly added to a solution of 5-fluoro-2-methoxy-phenylamine (61.5 g, 0.48 mol) in hydrochloric acid (20 % aqueous solution, 115 mL) at 0 C. After stirring for 10 minutes, a cooled (0 C) solution of acrolein (50 mL, 0.75 mol) in acetone (100 mL) containing calcium oxide (0.56 g, 0.010 mol) was added slowly to the reaction mixture. This was then followed by a solution of cuprous chloride (5 g, 0.05 mol) in acetone (100 mL) containing hydrochloric acid (20 % aqueous solution, 10 mL). The mixture was stirred at 0 to 30 C for 3 hours, and then extracted three times with dichloromethane (300 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil. The crude product was passed through a short silica column to give the crude product, which was used directly in the next step.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CLEVELAND, Thomas; MAKINGS, Lewis R.; HAMILTON, Matthew; GROOTENHUIS, Peter D.J.; WO2005/26137; (2005); A2;,
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These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)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. HPLC of Formula: C8H8Br2O

A mixture of B32.1 (4.3 g, 25mmol), CH3SNa (6.12 g, 4Smmol) in DMF (50 mL) was heated at 90 C for 18 h. DCM (50 mL) and water (100 mL) was added. The organic phase was separated andconcentrated to give the title compound (2.9 g, 80%). The crude product was used in the next step without further purification.

The synthetic route of 1-Bromo-4-(2-bromoethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
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20265-97-8, name is 4-Methoxyaniline hydrochloride, 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. category: ethers-buliding-blocks

General procedure: A cold solution of aryldiazonium salt (2.0 mmol) was preparedby adding a solution of NaNO2 (2.2 mmol, 0.15 g into 1.0 mL H2O) toa cold solution of arylamine hydrochloride (2.0 mmol of arylaminein 1.5 mL conc. HCl). The resulting solution of aryl diazonium saltwas added drop wise to a mixture of compound (II) (2.0 mmol,0.43 g) in water (15 mL) containing NaOH (25 mmol, 1.0 g) at0e5 C. The pH of the reaction mixture was maintained at 9e10 byadding 2.5% sodium hydroxide solution. Then, the reaction mixturewas stirred for 2 h at the same temperature and the precipitate wasfiltered off and the resulting solid was washed with cold ethanoland dried at 50 C in an oven. The crude product was purified usingthe recrystallization method as mentioned in Table 1. Under thesame reaction conditions, a series substituted arylazo quinolonedyes were obtained in satisfactory yields (Table 1, Scheme 2).

The synthetic route of 20265-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rufchahi, E.O. Moradi; Gilani, A. Ghanadzadeh; Taghvaei; Karimi; Ramezanzade; Journal of Molecular Structure; vol. 1108; (2016); p. 623 – 630;,
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