Month: March 2021

These common heterocyclic compound, 38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, 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. Quality Control of 1-Bromo-4-cyclopropoxybenzene

Step 1: A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for2 hours. The solution was quenched with NH4CI (aq. lmL) at-78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 x 15 mL). The organic layer was dried with anhydrous Na2504, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 mm (method 2), m/z = 162.8 [M +H].

The synthetic route of 1-Bromo-4-cyclopropoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
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Related Products of 6346-09-4, The chemical industry reduces the impact on the environment during synthesis 6346-09-4, name is 4,4-Diethoxybutan-1-amine, I believe this compound will play a more active role in future production and life.

3-(4,4-Diethoxy)-1,1-dimethylurea (IId). N,N-Dimethylcarbamoyl chloride (2.5 g) was added dropwise with cooling (5-7C) under argon to a solution of 3.74 g of 4,4-diethoxy-1-butanamine and4.77 g of triethylamine in 27 mL of benzene. The reaction mixture was stirred under cooling for 2 h. Then the precipitate was filtered off, the filtrate was evaporated in vacuum.

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, 4,4-Diethoxybutan-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Smolobochkin; Gazizov; Burilov; Pudovik; Russian Journal of General Chemistry; vol. 85; 7; (2015); p. 1779 – 1782; Zh. Obshch. Khim.; vol. 85; 7; (2015); p. 1217 – 1220,4;,
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Synthetic Route of 6876-00-2, 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 6876-00-2 as follows.

EXAMPLE 25 1-(4-Chlorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane A Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.33 g) in dry tetrahydrofuran (2 ml) and magnesium (30 mg) under nitrogen using iodine as an initiator at ca 40 C for 50 min, was cooled to room temperature then treated with cuprous bromide (ca 20 mg) for 10 min. After cooling to -78 C., a solution of 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropane (Example 17) (0.32 g) in tetrahydrofuran was added slowly with stirring, then the mixture was allowed to warm to room temperature overnight. The mixture was treated with water (4 ml), then extracted with diethyl ether (3*20 ml). The combined organic extracts were washed with water (2*10 ml), dried, and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(4-chlorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (98 mg, 22%).

According to the analysis of related databases, 6876-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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944561-44-8, name is 2-[2-(2-Propynyloxy)ethoxy]ethylamine, 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. Recommanded Product: 944561-44-8

Example 3: Synthesis of XZ-14424 Compound 7 (107 mg), amine 17 (84 mg), and DIPEA (193 muL) in 5 mL DMF were stirred at 85 C for 16 hours. Water was added to the reaction mixture and extracted with EtOAc. The organic phase was washed with water x1, brine x1, dried over Na2SO4, filtered and evaporated to dryness. The resulting mixture was purified by column chromatography using EtOAc and hexanes as eluents to afford 50 mg compound 18 as a green solid. Yield 32%. 1H NMR (400 MHz, CDCl3) delta 7.98 (s, 1H), 7.62-7.35 (m, 1H), 7.11 (d, J = 7.1 Hz, 1H), 6.93 (d, J = 8.5 Hz, 1H), 4.92 (dd, J = 11.9, 5.3 Hz, 1H), 4.21 (d, J = 2.3 Hz, 2H), 3.78-3.66 (m, 6H), 3.49 (t, J = 5.4 Hz, 2H), 2.93- 2.68 (m, 3H), 2.48-2.41 (m, 1H), 2.18-2.09 (m, 1H) ppm.

The synthetic route of 944561-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVENTURES, LLC; ZHENG, Guangrong; ZHOU, Daohong; ZHANG, Xuan; WANG, Yingying; CHANG, Jianhui; (269 pag.)WO2017/184995; (2017); A1;,
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Related Products of 589-10-6, These common heterocyclic compound, 589-10-6, name is (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.

EXAMPLE 2; PREPARATION OF 4-CHLORO-5-METHOXY-2-(2-PHENOXYETHYL)INDAN-l-ONE; 4-Chloro-5-methoxyindan-l-one (14.0 kg, 71.2 mol) (Example 1) was slurried in n- heptane (154 L). Glacial acetic acid (2.14 kg, 35.6 mol) was then added followed by 1,1- dimethylhydrazine (6.42 kg, 106.8 mol) such that the temperature remained <40C. The batch was then heated to 900C for 3 h. The batch was cooled to 600C, treated with THF (28 L) then concentrated to 40 L by distillation under atmospheric pressure. The resulting concentrate was cooled to 500C and diluted with THF (182 L). The THF solution was held overnight at <15C. The batch was cooled to -500C by direct injection of liquid N2, then n-hexyllithium (2.39 M in hexane, 21.2 kg, 71.2 mol) was added over 1.5 h, maintaining the internal temperature <-25C. The resulting slurry was aged between -30 and -200C for 30 min then a solution of beta-bromophenetole (14.4 kg) in THF (14 L) was added over 5 min, maintaining the internal temperature <-25C. The batch was then aged at -50C for 30 min. 6 N HCl (30 kg 37% HCl + 30 kg H2O) was charged to the mixture which was then aged at 500C until complete hydrolysis of the intermediate hydrazone was confirmed by HPLC (1.5 h). After cooling the batch to 200C, isopropyl acetate (56 L) was added and the aqueous layer was discarded. The organic phase was washed with water (75 L) then concentrated to 40 L using vacuum distillation at 4O0C. n-Heptane (40 L) was added and after aging for 30 min at 400C, 0.2% seed of the product ketone was added. The mixture was stirred for 1 h to allow a seed bed to develop, then a further 80 L of n-heptane was charged over 1 h at 400C. The resulting slurry was allowed to cool to 200C overnight then cooled to 5C over 1 h before filtering. The filter cake was washed with 4:1 heptanerisopropyl acetate (25 L), then sucked dry under a stream OfN2 for 3 h. The solid was dried in a vacuum oven at 45C for 48 h affording 20.2 kg of product as an off white solid in 88% yield. 1H NMR (400 MHz, CDCl3) delta 7.70 (IH, d, J = 8.4 Hz), 7.35-7.25 (2H, m), 7.04-6.88 (4H, m), 4.25-4.15 (2H, m), 4.00 (3H, s), 3.46-3.35 (IH, m)> 2.98-2.87 (2H, m), 2.54- 2.41 (IH, m), 2.03-1.89 (IH, m); 13C NMR (IOO MHz, CDCl3) delta 206J, 160.2, 158.8, 153.2, 130.8, 129.5, 123.6, 120.8, 119.7, 1 14.5, 111.6, 65.9, 56.8, 45.0, 32.2 <>31.0.

The synthetic route of 589-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2007/81895; (2007); A2;,
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Application of 106877-20-7, 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. 106877-20-7, name is 3-Methoxy-4-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

step 3-; A 100 mL round bottom flask fitted with a stir bar and septum was charged with 84a (3.01) g and maintained nitrogen atmosphere. To the flask was added anhydrous dioxane (25 mL) and HOAc (7.5 mL). The solution was stirred rapidly in an ice bath and a solution of bromine and dioxane (20 mL, 0.135 g Br2/mL) was added dropwise over 30 min using a syringe pump. A beige precipitate formed and the mixture thickened. The ice bath was removed and the reaction mixture stirred at RT for 1 h. The reaction mixture was poured into a mixture of 1.0 M NaOH (150 mL) and 2.0 M Na2CO3 (150 mL) and extracted with DCM (3¡Á100 mL). The combined extracts were washed sequentially with 0.5 M Na2CO3 (150 mL) and brine (150 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting pale yellow liquid slowly solidified and darkened to afford 84b (4.10 g) black crystalline solid.

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; de Vicente Fidalgo, Javier; Li, Jim; Schoenfeld, Ryan Craig; Talamas, Francisco Xavier; Taygerly, Joshua Paul Gergely; US2010/311760; (2010); A1;,
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These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-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. COA of Formula: C15H23BrO

Production Example 7 of Optically Active AminoalcoholA 300 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.99 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 25.30 g of 4-methoxy-3,5-di-tert-butylbromobenzene and 119.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10 C., 1.45 g of L-alanine methyl ester hydrochloride was added. The temperature of the resulting mixture was raised to room temperature, and the mixture was further refluxed for 3 hours. The resulting reaction mixture was cooled to 0 to 5 C. To the reaction mixture were added dropwise 70.0 mL of an aqueous saturated ammonium chloride solution, and further 20.0 mL of water. The resulting mixture was stirred at 20 C. for 12 minutes. The resulting mixture was extracted with 70.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9830/70) to obtain 3.32 g of a pale yellow solid of (S)-2-amino-1,1-di(4-methoxy-3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.49 (2H, s), 7.34 (2H, s), 4.01 (1H, m), 3.86 (1H, brs), 3.67 (3H, s), 3.66 (3H, s), 1.44 (18H, s), 1.42 (18H, s), 1.22 (2H, br.s), 0.94 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 158.58, 158.29, 143.46, 142.94, 141.10, 139.19, 124.95, 124.84, 79.58, 64.76, 53, 42, 36.58, 36.50, 32.91, 21.75, 18.07

The synthetic route of 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
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Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-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.

To a solution of 3-bromo-5-fluoroanisole (250 mg, 1.22 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (32 mg, 1.28 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After cooling down to room temperature, 6-bromopyridin-2-yl carboxaldehyde (271 mg, 1.47 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 80 C overnight. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was purified by column chromatography (hexane/ethyl acetate 8:2) to afford the analytically pure compound in 21% yield (80 mg). C13H11BrFNO2; MW 312; 1H NMR (acetone-d6): delta 7.74 (t, J = 7.6 Hz, 1H), 7.64-7.61 (m, 1H), 7.47 (dd, J = 0.9 Hz, J = 7.2 Hz, 1H), 6.92-6.90 (m, 1H), 6.81 (ddd, J = 0.6 Hz, J = 1.3 Hz, J = 9.1 Hz, 1H), 6.59 (dt, J = 2.5 Hz, J = 10.7 Hz, 1H), 5.77 (d, J = 4.7 Hz, 1H), 5.35 (d, J = 4.7 Hz, 1H), 3.79 (s, 3H); 13C NMR (acetone-d6): delta 165.8, 165.3, 140.8, 127.5, 120.3, 109.4, 106.1, 105.9, 101.0, 100.8, 75.8, 56.0; LC/MS m/z: 312-314 (M + H)+.

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-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Article; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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Related Products of 887581-09-1,Some common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, molecular formula is C8H10BrNO, 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.

General procedure: To a magnetically stirred solution of the formyl ester 8a (400 mg, 1.6 mmol) in CH2ClCH2Cl (5 mL) at room temperature, were added sequentially 2-bromobenzyl amine 3a (420 mg, 2.2 mmol) and AcOH (0.14 mL, 2.4 mmol) followed by refluxing of the mixture for 12 h. After cooling, the reaction mixture was treated with aqueous NaHCO3 solution and extracted with ethyl acetate (3 ¡Á 12 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Concentration of the filtrate followed by flash chromatography (ethyl acetate/hexane, 1:6 to 2:3) furnished the cyclic enamide 9aa (480 mg, 80%) as brown viscous oil.

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

Reference:
Article; Satyanarayana, Gedu; Maier, Martin E.; Tetrahedron; vol. 68; 6; (2012); p. 1745 – 1749;,
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Electric Literature of 1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Representative procedure for the 2-methyl-N,4-diphenylquinoline-3-carboxamide (Entry 22, Table 1): To the magnetically stirred solution of KOt-Bu (2 mmol) in THF (6 mL) at rt, was added methyl 2-methyl-4-phenylquinoline-3-carboxylate 3a (0.277 g, 1 mmol) followed by addition of aniline (0.093 mL, 1 mmol, 1 equiv) and the mixture was allow to stirred at rt until the completion of reaction (5 h, monitored by TLC) . After completion of reaction THF evaporated under rotary vacuum evaporation, crude reaction mixture was extracted with EtOAc (3 ¡Á 5 mL) and H2O (5 mL). The combined EtOAc extracts were dried (anh Na2SO4), filtered, and the filtrate was concentrated under rotary vacuum evaporation. The crude product was adsorbed on silica gel (230-400 mesh size, 500 mg), charged on to a flash chromatography column of silica-gel (230-400 mesh size, 2.5 g), and eluted with hexane-EtOAc (90:10) to obtain analytically pure 2-methyl-N,4-diphenylquinoline-3-carboxamide, 5a as white solid (0.219 g, 65%);

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

Reference:
Article; Tanwar, Babita; Kumar, Asim; Yogeeswari, Perumal; Sriram, Dharmarajan; Chakraborti, Asit K.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 24; (2016); p. 5960 – 5966;,
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