Tag: M.W=200-300

20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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. Formula: C8H9BrO2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 C. and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted, DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed through a through a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100% ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70% purity). MS (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)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 5414-19-7, COA of Formula: C4H8Br2O

General procedure: 1,3-Dibromopropane (2.2 Kg, 10.9 mol) was slowly added to a stirred suspension of 264 g magnesium turnings (11 mol)In tetrahydrofuran (17.6 L).Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition is complete, the mixture is precooled to minus 50 degrees Celsius for two hours at minus 40 to 50 degrees Celsius,And the reaction mixture prepared from 2-chloropyridine was added.Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition was completed, the temperature was slowly raised to 60 C and stirred for 3 hours.The reaction mixture was concentrated under reduced pressure to 20 liters of n-hexane (20 L).The resulting solid was removed by filtration.Concentration of the filtrate followed by pressure distillation gave the desired target intermediate (1.16 Kg, 62%) as a colorless liquid.

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Reference:
Patent; Zhejiang Xingyue Pharmaceutical Technology Co., Ltd.; Ying Lv; Chen Qingquan; Hu Junbin; (103 pag.)CN104177394; (2017); B;,
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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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 4316-51-2

POCl3 (6 mL, 64.17 mmol) was carefully added to a solution of 4-methoxy-N,N-diphenylaniline (10 g, 36.32 mmol), DMF (5 mL, 64.85 mmol) and 50 mL of 1,2-dichloroethane. The mixture was refluxed for 4 h, then cooled to room temperature (r.t.), and poured into a saturated aqueous sodium acetate solution (100 mL). The product was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated by a rotary evaporator. The residue was purified by silica gel column chromatography using ethyl acetate: n-hexane (2:3) to give (1) (7.6 g, Yield: 69%). TOF/MS (ESI): found 326.1 (M+Na+). 1H NMR (300 MHz, CDCl3, delta): 9.79 (s, 1H, ArCHO), 7.68-6.89 (m, 14H, ArH), 3.83 (s, 3H, ArOCH3).

According to the analysis of related databases, 4316-51-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Giang, Ha Ngoc; Kinashi, Kenji; Sakai, Wataru; Tsutsumi, Naoto; Journal of Photochemistry and Photobiology A: Chemistry; vol. 291; (2014); p. 26 – 33;,
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Synthetic Route of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 °C for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 °C, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Bromopropoxy)benzene, its application will become more common.

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, Safety of 1-Bromo-3-fluoro-5-methoxybenzene

A solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1 H-pyrazol-4-ylboronic acid (41 mg, 0.083 mmol), 1-bromo-3- fluoro-5-methoxybenzene (20 mg, 0.10 mmol), Pd(PPh3)4 (10 mg, 0.0083 mmol), Na2003 (44 mg, 0.42 mmol) in degassed 1,4-dioxane and H20 (4:1, 1.7 mL) was heated at 85 C for 18 hours. LiOH (10 mg, 0.42 mmol) was added and the reaction was heated at 95 O under microwave radiation for 30 mm. i N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of ammonium formate) (60 to 80%). The product was lyophylised to give the title compound (16 mg, 0.028 mmol, 34%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 1.8 Hz, 1H), 8.03 (dd, J= 8.5, 1.8 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 6.94 -6.89 (m, 2H), 6.86 (d, J = 11.5 Hz, 1 H), 3.80 (5, 3H),3.35 (sept, J = 6.7 Hz, 1H), 2.32 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz): 552.1 [M+1].

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-Bromo-3-fluoro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
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Related Products of 886762-08-9, 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. 886762-08-9 name is 5-Bromo-2-(trifluoromethoxy)aniline, 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.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
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Electric Literature of 43229-65-8, The chemical industry reduces the impact on the environment during synthesis 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, I believe this compound will play a more active role in future production and life.

1) A compound of the formula II (178.1 g) and a compound of the formula III (161.7 g) are added to a reaction flask and stirred.Heat to internal temperature 90-100 C, reaction 2-3h, to internal temperature 120-130 C, reaction 2-3h to complete(HPLC detection, the peak area is calculated according to the normalization method, and the compound of the formula III is less than 10%, the reaction is considered complete), and the compound of formula IV is obtained, 320.5g,After cooling to 70 ± 5 C, it was dissolved in anhydrous ethanol (220 mL) to prepare for the next step.

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, N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Health Yuan Breathe Pharmaceutical Engineering Co., Ltd.; Shanghai Fangyu Health Pharmaceutical Technology Co., Ltd.; Yu Xiong; Xiao Duzheng; Zheng Guangji; Chen Yuhua; Yuan Xilun; (28 pag.)CN109535027; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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 116557-46-1, Recommanded Product: 116557-46-1

A suspension of 3-bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg, 2.97 mmol) and potassium acetate (729 mg, 7.42 mmol) in 1,4-dioxane (8 mL) was sparged with nitrogen for 5 min. Pd(dppf)Cl2·DCM (173 mg, 0.21 mmol) was added and the mixture was heated under reflux for 2.5 h then cooled to room temperature. The reaction was diluted with DCM (35 mL) and washed with water (35 mL). The organic phase was concentrated under reduced pressure then purified by flash column chromatography, eluting with 0-100% EtOAc in isohexane, to return 49h (358 mg, 58%) an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 6.72-6.83 (m, 3H), 4.80 (s, 2H), 3.64 (s, 3H), 1.28 (s, 12H).

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:
Article; Newton, Rebecca; Bowler, Katherine A.; Burns, Emily M.; Chapman, Philip J.; Fairweather, Emma E.; Fritzl, Samantha J.R.; Goldberg, Kristin M.; Hamilton, Niall M.; Holt, Sarah V.; Hopkins, Gemma V.; Jones, Stuart D.; Jordan, Allan M.; Lyons, Amanda J.; Nikki March; McDonald, Neil Q.; Maguire, Laura A.; Mould, Daniel P.; Purkiss, Andrew G.; Small, Helen F.; Stowell, Alexandra I.J.; Thomson, Graeme J.; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 20 – 32;,
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Adding a certain compound to certain chemical reactions, such as: 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, 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 22171-15-9, SDS of cas: 22171-15-9

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.6g, 3.92mmol), triethylamine (1.64mL, 11.8mmol) and benzotriazole-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (2.6g, 5.9mmol) were dissolved in N,N-dimethylformamide (200mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (1.25g, 5.9mmol) was added thereto, and the solution was stirred at room temperature for 16 hours. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate : hexane = 2 : 1, then ethyl acetate), the resulting solid was washed with solvent (chloroform : ethyl acetate = 2 : 1), and the title compound (0.37g, 1.1 mmol, 27%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.29 (2H, d, J=6.0Hz), 5.07 (2H, s), 5.66 (1H, d, J=8.4Hz), 6.06 (2H, br s), 6.91-6.97 (4H, m), 7.19 (2H, d, J=8.8Hz), 7.29-7.45 (5H, m), 7.65 (1H, d, J=8.4Hz), 8.27 (1H, t, J=6.0Hz).

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-(Benzyloxy)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Recommanded Product: 74137-36-3

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole percent, 20.66 mg), triphenylphosphine (4 mole percent, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32percent (751 mg). C10H9Br3O; MW 256/258; 1H-NMR (CD3OD): delta 7.61 (d, J=16.1 Hz, 1H), 7.38-7.37 (m, 1H), 7.17-7.16 (m, 2H), 6.53 (d, J=16.1 Hz, 1H), 3.87 (s, 3H); 13C-NMR (CD3OD): delta 169.8, 162.3, 144.5, 138.9, 124.2, 121.4, 120.0, 113.4, 56.2

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, 1,3-Dibromo-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
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