Tag: M.W=200-300

Electric Literature of 14804-31-0, The chemical industry reduces the impact on the environment during synthesis 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 109; Preparation of 2-Amino-5-(4-methoxy-3-methyl phenyl)-3-methyl-5-(2-phenylpyridin-4-yl)-3,5-dihydro-4H-imidazol-4-one; Step a) [(4-Methoxy-3-methylphenyl)ethynyl](trimethyl)silane; A solution of 4-bromo-1-methoxy-2-methylbenzene (6.702 g) in toluene was treated with tetrakis(triphenylphosphie)palladium (0) (1.15 g), followed by diisopropylamine (23 mL), trimethylsilyl acetylene (4.7 mL) and copper iodide (I) (0.127 g). The reaction was heated at 45 C. in nitrogen atmosphere overnight and evaporated to dryness. The resultant residue was applied on a large silica pad and eluted with hexane:ethyl acetate (2:1). The elute was evaporated to dryness to give the silane intermediate as a brown oil (7.167 g). The compound was characterized by LCMS analysis. LCMS Conditions: HP 1100 HPLC system; Waters Xterra MS C18, 2 mm (i.d.)×50 mm (length), 3.5 um column, set at 50 C.; Flow rate 1.0 mL/min; Solvent A: 0.02% NH4OH in water; Solvent B 0.02% NH4OH in ACN; Gradient: Time O: 10% B; 2.5 min 90% B; 3 min 90% B; Sample concentration: 2.0 mM; Injection volume: 5 uL; Detection: 220 nm, 254 nm DAD

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-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2007/4730; (2007); A1;,
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Application of 261762-35-0, These common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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.

In a 50 mL round-bottom flask, introduce 1 g (4.48 mmol) of 5-bromo-2,3-difluoroanisole in 25 mL of dioxane then add 1.708 g (6.73 mmol) of bis(pinacolato)diboron, 1.320 g (13.45 mmol) of potassium acetate and 0.183 g (0.224 mmol) of bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The reaction mixture is stirred at 80 C. overnight. After returning to room temperature, the reaction is hydrolyzed by slow addition of water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 95:5) to afford 197 mg (15%) of intermediate 13 as a yellow solid. (0484) LCMS (EI, m/z): (M+1) 271.08 (0485) 1H NMR: dH ppm (400 MHz, DMSO): 7.13-7.17 (2H, m, CHarom), 3.90 (3H, m, CH3), 1.30 (12H, m, CH3).

The synthetic route of 261762-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; GRISONI, Serge; GOMES, Bruno; SCHMITT, Philippe; (43 pag.)US2017/281622; (2017); A1;,
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Some common heterocyclic compound, 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. Computed Properties of C8H8Br2O2

Add to the dry three-necked flask with a magnetic rotor 1,3-dibromo-4,6-dimethoxybenzene (3.0515 g, 10 mmol, 97%, 1.0 eq),4-biphenylboronic acid (4.4449 g, 22 mmol, 98%, 2.2 equivalents),palladium acetate (0.0674g, 0.3mmol,0.03 equivalents) and the ligand S-Phos (0.2513 g, 0.6 mmol, 98%, 0.06 equivalents).Nitrogen gas was distilled off three times, and then an aqueous solution (20 mL) of 1,4-dioxane (60 mL) and potassium carbonate (6.9100 g, 50 mmol, 5.0 eq. The three vials were then placed in a 110 C oil bath. After stirring for 24 hours, the reaction was monitored by thin layer chromatography. After cooling to room temperature, the organic phase was separated and aqueous was extracted with ethyl acetate (30mL×2).The organic phases were combined, dried over anhydrous sodium sulfate, filtered and evaporated.The crude product was separated and purified by flash column chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 50/1) to give A5, white solid 4.4216g, 99% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24988-36-1, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Li Guijie; Dai Jianxin; Chen Shaohai; Feng Qi; (28 pag.)CN110183476; (2019); A;,
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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

A. 1H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide DIEA (9.3 mL, 53.4 mmol) was added to a solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), indazole-3-carboxylic acid (2.89 g, 17.8 mmol) and HBTU (7.1 g, 18.7 mmol) in DMF (60 mL), and the resulting solution was stirred at ambient temperature for 24 hours. The solution was heated to 70 C for 4 hours, and then poured into a mixture of saturated aqueous sodium bicarbonate on ice. The product, an off white solid, 6.0 g, was collected by filtration, washed with water and used without further purification in the subsequent reaction. MS m/z344 (MH+).’H NMR (DMSO-d6) 8 5.11 (s, 2H), 7.02 (d, 2H), 7.26-7. 48 (m, 7H), 7.67 (d, 1 H), 7.75 (d, 2H), 7.81 (d, 1 H), 8. 24 (d, 1 H) and 10.24 (s, 1H).

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; JANSSEN PHARMACEUTICA N.V.; WO2005/84663; (2005); 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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Roundbottom flask is charged with 5-bromo-2-methylaniline( 400.00 mg; 2.15 mmol; 1 .0 eg.), triethylamine ( 330.76 mL; 2.36 mmol; 1.1 eq.) and anhydrous dichloromethane (12 mL). Acetyl chloride ( 185.64 mg; 2.36 mmol; 1.1 eq.) is then added dropwise and reaction mixture is stirred at room temperature for 24h. After this time diethyl ether (24 mL) is added and mixture is washed with saturated aqueous solution of ammonium chloride (2×20 mL) and brine (2×20 mL). Organic layer is then dried over anhydrous Na2SO4 overnight. The second organic solvent is evaporated to afford N-(5- bromo-2-methylphenyl)acetamide (513.20 mg; yield 93.5 %; 89.3 % by UPLC) as brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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Electric Literature of 10385-36-1, A common heterocyclic compound, 10385-36-1, name is 1-Bromo-2,3,4-trimethoxybenzene, molecular formula is C9H11BrO3, 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.

The title compound was prepared according to the procedure described for 10, starting from compound 19a. Colorless oil (crude). This was used in the next step without further purification

The synthetic route of 10385-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Masaharu; Kajita, Daisuke; Matsumoto, Yotaro; Hashimoto, Yuichi; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7381 – 7391;,
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588-96-5, name is p-Bromophenetole, 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. Safety of p-Bromophenetole

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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Some common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: C7H5BrF3NO

b) 5-Bromo-2-trifluoromethoxyphenol A solution of 210 mmol of sodium nitrite in 120 ml of water is added dropwise to a suspension of 200 mmol of 5-bromo-2-trifluoromethoxyaniline in 500 ml of ethanol and 50 ml of conc. HCl at 0C. The reaction mixture is stirred at 5C for 1.5 hours. The reaction mixture is slowly added dropwise to a solution of 135 ml of conc. sulphuric acid in 2.8 l of water and stirred under reflux overnight. The reaction mixture is extracted with diethyl ether (3x) – the combined organic phases are washed with water and 1 M sodium bicarbonate solution and then extracted with 2N NaOH (2x). The combined aqueous phases are acidified with conc. HCl and extracted with diethyl ether (3x). The combined organic phases are washed with water, dried with sodium sulphate and evaporated. The crude title compound is obtained from the residue.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 886762-08-9, its application will become more common.

Reference:
Patent; Speedel Experimenta AG; EP1958666; (2008); A1;,
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Related Products of 202865-80-3, A common heterocyclic compound, 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, molecular formula is C9H10BrFO, 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 2-amino-5-ethyl-3-(4-methylphenoxy)pyrazine (55.0 mg, 0.240 mmol) and dioxane (1 mL) were added 4-bromo-2-fluoro-1-isopropoxybenzene (61 mg, 0.26 mmol), tris(dibenzylideneacetone)(0) (2.8 mg, 0.0030 mmol), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (4.2 mg, 0.0072 mmol) and sodium phenoxide trihydrate (61 mg, 0.36 mmol), and the resulting mixture was heated at reflux for 4 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed by brine, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by reversed-phase HPLC (0.3% formic acid/acetonitrile) to give 5-ethyl-2-(3-fluoro-4-isopropoxyphenylamino)-3-(4-methylphenoxy)pyrazine (17 mg, Yield: 18%) as pale brown solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.05 (3H, t, J=7.5 Hz), 1.26 (6H, d, J=5.8 Hz), 2.33 (3H, s), 2.44 (2H, q, J=7.5 Hz), 4.45-4.52 (1H, m), 705-7.17 (3H, m), 725 (2H, d, J=8.6 Hz), 7.55-7.61 (1H, m), 7.69 (1H, s), 7.85-7.91 (1H, m), 8.93 (1H, s).

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; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
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51388-20-6, name is 4-(Benzyloxy)aniline 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. HPLC of Formula: C13H14ClNO

4-{[4-(Benzyloxy)phenyI]amino}-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide; 2-fert-Butyl-4-chloro-5~phenylisothiazol-3(2H)-one 1,1-dioxide (0.3g, 1 mmol), 4- benzyloxyaniline hydrochloride (0.307g, 1.3 mmol) and TEA (0.304g, 3 mmol) was dissolved in dry DMSO (10 ml). The reaction was heated at 110 C for 25 min in a microwave reactor. The reaction mixture was diluted with water (200 ml) and extracted with EtOAc (200 ml), the organic phase was dried (MgSO4), filtered and evaporated. The residue was purified by silica gel column chromatography using a 65:35 mixture of heptane:EtOAc as eluant to give the title compound (0.345 g, 75 %).

The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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