Author: Jessica.F

1484-26-0, name is 3-Benzyloxyaniline, 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: C13H13NO

4-Chloro-6-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7Hpyrrolo-[2,3-d]pyrimidine [8] (600 mg, 1.46 mmol) and 3-(benzyloxy)aniline (585 mg, 2.94 mmol) were dissolved in nbutanol(12 mL) under an N2-atmosphere. The reaction mixturewas agitated at 100 °C for 6.5 hours. Following work-up asdescribed in Section 2.4.1, the crude product was purified twiceby silica-gel column chromatography (n-pentane/THF, 9/2, Rf = 0.37). Drying gave 661 mg(1.15 mmol, 79percent) of a orange solid.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reiers°lmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
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Reference of 5111-65-9, 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.

SYNTHESIS EXAMPLE 1; According to a reaction path of Reaction Scheme 1, compound 19 represented by Formula 19 was synthesized: Synthesis of Compound 19; Synthesis of Intermediate A; 7.5 g (32 mmol) of 2-bromo-6-methoxynaphthalene, 4.6 g (25 mmol) of phenoxazine, 3.7 g (38 mmol) of sodium tert-butoxide ((t-BuO)Na), 0.3 g (0.33 mmol) of Pd2(dba)3 [(tris(dibenzylidine acetone) dipalladium (0))], and 0.11 g (0.55 mmol) of tri(tert-butyl)phosphine were dissolved in 125 mL of toluene and were reacted for 12 hours at 80 C.After the reaction was completed, the reaction mixture was cooled down to an ambient temperature and 200 ml of distilled water was added and quenched. Then, xylene and water were extracted in the volume ratio of 1:1.The collected organic layer was dried and concentrated using MgSO4 and a column chromatography was performed using an eluant formed of toluene and hexane in the volume ratio of 1:2. The obtained effluent was concentrated and dried to obtain 6.8 g (Yield: 80%) of intermediate A. The structure of intermediate A was identified through 1H NMR spectroscopy.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-methoxynaphthalene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Son, Jhun-Mo; Yu, Eun-Sun; Kwon, O-Hyun; Son, Young-Mok; Kim, Yu-Jin; US2007/176541; (2007); A1;,
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Related Products of 332-48-9, A common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

b) 2-({4-Bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2- methyl-propionic acid methyl esterTo 90 mg cesium carbonate and 92 mg 2-[(4-bromo-1-hydroxy-naphthalene-2- carbonyl)-amino]-2-methyl-propionic acid methyl ester in 1 ml abs. DMF 60 mg 4- fluorophenoxyethylbromide was added. After 16 h at room temperature the reaction was poured unto ice-water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. After purification by RP-HPLC 61 mg of 2-({4-Bromo-1-[2-(4- fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester were obtained. _ _ _ . . _ – – c24H23BrFNO5 (504.36), LCMS (ESI): 504.05, 506.05 (MH+, bromo-pattern).

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; SANOFI-AVENTIS; WO2008/409; (2008); A1;,
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Application of 82830-49-7,Some common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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 an oven-dried round-bottom flask with a stir bar were charged with a solution of secondary amines 2 (1.5 mmol) in 1 mLdry THF at room temperature under an argon atmosphere. To thissolution was slowly added 1.2 mL nBuLi (2.5 mol/L in n-hexane,3.0 mmol) via syringe. After stirring at 25 C for 10 min, a solution of fluoroarene 1 (1.0 mmol) in 1mL dry THF was added to the reaction flask. The reaction mixture was stirred for 0.5 h at 25 C, and then quenched with 2 mL saturated aqueous solution of NaCl and extracted with H2O (20 mL) and ethyl acetate (3 20 mL). The organic layer was separated and dried with anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using a petroleum ether/ethyl acetate mixture as eluent to afford the pure target compounds.

The synthetic route of 82830-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Yingyin; Li, Meng; Ji, Xinfei; Wu, Jingjing; Cao, Song; Tetrahedron; vol. 73; 11; (2017); p. 1466 – 1472;,
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Synthetic Route of 80936-82-9,Some common heterocyclic compound, 80936-82-9, name is 4-(Methoxymethyl)aniline, molecular formula is C8H11NO, 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.

5.3b (1.1 g, 8.02 mmol, 1.0 equiv) was dissolved in acetone: water (2:1, 9 mL) and cooled toO C. NaHCO3 (1.42 g, 16.86 mmol, 2.1 equiv) and CBZ-Cl (1.78 g, 10.44 mmol, 1.3 equiv) were added and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a residue. The residue was purified by silica gel column chromatography (2-5 % EtOAc in Hexane) to afford product 5.3c (1.56 g, 72 % yield). 1H NMR (400 MHz, DMSO) 6 9.80 (s, 1H), 7.49-7.38 (m, 6H), 7.23 (t, J= 6.5 Hz, 2H), 5.15 (s, 2H), 4.32 (s, 2H), 3.25 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Methoxymethyl)aniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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 54149-17-6, HPLC of Formula: C5H11BrO2

Example 83 Preparation of 17-[2-(2-methoxyethoxy)ethyl]-N-(pyridin-3-yl)morphinan-3-amine (83), hydrochloride salt Step 1 : Preparation of 17-[2-(2-etaiotabeta1iotaomicronchigamma61iotaomicronchinu)61iotagamma1]etaiotaomicronphi1iotaeta3eta-3-gamma1 trifluoromethanesulfonate, The acetonitrile solution of morphinan-3-yl trifluoromethanesulfonate (2.7 g, 7.19 mmol), l-bromo-2-(2-methoxyethoxy)ethane (2.6 g, 14.4 mmol) and cesium carbonate (2.6 g, 43.2 mmol) was heated at 50 C for 18 hours. After cooling the mixture to room temperature, all solvent was removed and the reaction mixture was extracted with dichloromethane twice. The solvent was evaporated and the residue was purified by silica gel chromatography using Biotage with dichloromethane/methanol eluents. 17-[2-(2- Methoxyethoxy)ethyl]morphinan-3-yl trifluoromethanesulfonate was obtained as a light- yellow liquid (2.5 g, 73% yield), MS (EI) for C22H30F3NO5S: 478.2 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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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Synthetic Route of 929-75-9, 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 929-75-9 as follows.

General procedure: The diamine 10 (1 equiv) in DCM solution (10 mL / mmol) was treated with Boc2O in default (0.15 equiv) for 5 h at 0 C and 18 h at room temperature. The organic phase was washed with water, until all the unreacted 10 was extracted. The Boc-protected compound 11 was quantitatively recovered after drying (MgSO4) and concentration under vacuum. 11a: 1H NMR (300 MHz, CDCl3): d 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2). 11b: 1H NMR (300 MHz, CDCl3): d 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).

According to the analysis of related databases, 929-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Favre, Annaick; Grugier, Jerome; Brans, Alain; Joris, Bernard; Marchand-Brynaert, Jacqueline; Tetrahedron; vol. 68; 52; (2012); p. 10818 – 10826;,
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Related Products of 1462-37-9, The chemical industry reduces the impact on the environment during synthesis 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, I believe this compound will play a more active role in future production and life.

Methyl 1-(2-(benzyloxy)ethyl)-2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate To a suspension of NaH (14 mg of 60percent dispersion in mineral oil, 0.354 mmol) in DMF (2 mL), methyl 2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate (130 mg, 0.295 mmol) was added and the reaction mixture was stirred at rt for 15 min. Benzyl 2-bromoethyl ether (0.052 mL, 0.325 mmol) was then added, and the reaction mixture was stirred at rt overnight before being quenched by the addition of water. The resultant mixture was extracted with ethyl acetate (2*20 mL) and the organic layers were combined, washed with 1N HCl solution, and then dried (MgSO4), filtered and concentrated under vacuum. The residue was then purified by Prep. reverse phase HPLC to give the title compound as light yellow solid (83.5 mg, 49percent yield). MS m/z 575(MH+); 1H NMR (500 MHz, CDCl3) delta ppm 1.21-1.31 (m, 3 H) 1.69-1.90 (m, 7 H) 2.53 (m, 1 H) 3.65 (m, 1 H) 3.72 (m, 1 H) 3.92 (s, 3 H) 4.17 (m, 1 H) 4.27 (m, 1 H) 4.32 (s, 2 H) 5.21 (s, 2 H) 6.18 (t, J=6.87 Hz, 1 H) 7.07-7.12 (m, 2 H) 7.21-7.36 (m, 9 H) 7.41 (dd, J=6.71, 2.14 Hz, 1 H) 7.74 (dd, J=8.54, 1.22 Hz 1 H) 7.78 (m, J=8.55 Hz, 1 H) 8.12 (s, 1 H).

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, ((2-Bromoethoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 707-07-3, name is (Trimethoxymethyl)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 707-07-3, name: (Trimethoxymethyl)benzene

A mixture of methyl 1-acetyl-oxindole-6-carboxylate of formula 3 (7.00 g), toluene (20 ml) and acetanhydride (9.8 ml) was stirred in a flask equipped with a small Vigreux column and adistillation adapter at 110C for 5 mm, producing a turbid orange-red solution. At the temperature of 110C, trimethyl orthobenzoate (12.4 ml) was added dropwise to the reaction mixture, followed by toluene (16 ml), by means of a syringe fitted with a needle reaching into the flask. The bath temperature was slowly increased to slowly distil the produced methyl acetate. After distilling for 4 h, the bath temperature was 125C and the distillate volume was6.5 ml. The reaction mixture was left to stand at 20C for 4 h and the crystallization of the product was completed in 2 h at 10C. The product was filtered off, washed with toluene and finally with a mixture of toluene and ethyl acetate (1: 1). The yield was 8.94 g (85%) of a beige powder

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, (Trimethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENTIVA, K.S.; MECA, Ludek; (16 pag.)WO2017/16530; (2017); A1;,
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Application of 2216-69-5, 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. 2216-69-5, name is 1-Methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the solution of anisole (0.50 g, 4.6 mmol), TBAB (0.75 g, 2.3 mmol), KBr (0.83 g, 6.9 mmol), ethyl acetate (3.0 mL) and water (0.050 g, 2.8 mmol) were added and stirred at room temperature. A solution of BTC (1.78 g, 6.0 mmol) in ethyl acetate (6.0 mL) was dropwised to the reaction mixture. After the reaction finished, the reaction mixture was washed with water (10 mL × 2) and evaporated. The product was obtained with 99% purity by HPLC. 1 H NMR (400 MHz, DMSO-d6, ppm): delta 7.46-7.42 (m, 2H), 6.78-6.76 (m, 2H), 3.74 (s, 3H).

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-Methoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Yingzhou; Hu, Dufen; Zheng, Hui; Mei, David; Gao, Zhaobo; Tetrahedron; vol. 75; 39; (2019);,
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