Tag: M.W=200-300

Electric Literature of 13633-25-5,Some common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, molecular formula is C10H13Br, 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.

lambda/-{2-r(3-phenylbutoxyphenylVphenyl- aminolethvDacetamide (5i): A mixture of lambda/-(3-hydroxyphenyl)aniline (2.7 mmol) and 1-bromo-4-phenylbutane (2.02 mmol) was refluxed for 5 h in a 10% ethanol solution of KOH. The reaction mixture was cooled to room temperature, poured into water and extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated under reduced pressure to provide a residue which was purified by flash chromatography (silica gel; cyclohexane/EtOAc, 8:2 as eluent). Yield lambda/-(3-phenylbutoxyphenyl)-aniline (3i): 86%; oil; EI-MS 317 (M+), 91 (100); 1H-NMR (CDCI3): delta 1.83 (m, 4H), 2.68 (m, 2H), 3.96 (m, 2H), 5.75 (br, 1 H), 6.46-7.38 (m, 14H).

The synthetic route of 13633-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MCGILL UNIVERSITY; UNIVERSITA DEGLI STUDI DI PARMA; UNIVERSITA DEGLI STUDI DI MILANO; UNIVERSITA DEGLI STUDI DI URBINO; WO2007/79593; (2007); A1;,
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Application of 4549-33-1, 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 4549-33-1 as follows.

DIEA (259 mg, 2 mmol) and 1,9-dibromoctane (286 mg,1 mmol) were added to the mixture whichincluded compound 1a (508 mg, 2 mmol) in toluene/ethanol (EtOH) (1:1) (60 mL), followed by refluxfor 48 h. The solvent was removed under vacuum. The process of this reaction was controlled byLC-MS and TLC. For TLC control and purification, the DCM/MeOH (7/1) system was used. Neutralalumina oxide was used to purify the product (yield 50%). LC-MS: [M + H]+ = 633. 1H NMR (500 MHz, MeOD): delta = 1.31(m, 2H, CH2), 1.41 (m, 12H, 6xCH2), 2.20 (m, 4H, 2xCH2),3.04 (m, 4H, 2xNHCH2), 3.13 (m, 4H, 2xNHCH2), 3.89 (d, J = 10.3 Hz, 4H, 2xNCH2) 7.86 (t, J = 7.8 Hz,4H, ArH), 8.41 (d, J = 8.1 Hz, 4H, ArH), 8.60 (d, J = 7.1 Hz, 4H, ArH) ppm.13C NMR (125 MHz, CDCl3): delta = 22.3 (CH2), 23,2 (CH2), 26,5 (CH2), 27,1 (CH2), 28.7 (CH2),37.9 (CH2), 46.5 (CH2), 48,6 (CH2), 122.3 (Caro), 127.2 (CaroH), 127.3 (Caro), 130.7 (CaroH), 131.3 (Caro),134.3 (CaroH), 163.5 (C=O) ppm.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Keskin, Elif; Ucisik, Mehmet Hikmet; Sucu, Bilgesu Onur; Guzel, Mustafa; Molecules; vol. 24; 24; (2019);,
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Electric Literature of 2576-47-8, 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 2576-47-8 as follows.

General procedure: The different arylsulfonyl chloride 2a-s (4 mmol) and 3-bromopropylamine hydrobromide (3) (4.6mmol) or 2-bromoethylamine hydrobromide (4) (4.6 mmol) were suspended in anhydrous DCM (14 mL)under nitrogen atmosphere. The reaction mixture was cooled to 0C in an ice-bath and then treateddropwise with triethylamine (1.34 mL, 9.6 mmol) over a period of 10 min. The reaction mixture wasstirred for 10 min under ice-cooling, then diluted with DCM (50 mL) and washed with 2M hydrochloricacid solution (2 x 60 mL) and brine (2 x 60 mL). The organic solvent was evaporated at reduced pressureafter drying over MgSO4.

According to the analysis of related databases, 2576-47-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Courtney-Smith, Matthew; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1115 – 1131;,
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Application of 393-36-2,Some common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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. 6-Bromo-3-(ethyl oxalamido)benzotrifluoride To a stirred solution of 3-amino-6-bromobenzotrifluoride (2.40 g, 10.00 mmol, Aldrich) in dried THF (10 mL) and triethylamine (1 mL) in an ice bath was dropwise added ethyl oxalyl chloride (1.7 mL, 16 mmol, Aldrich). The resulting yellow suspension was stirred at 25 C. for 3 h and it was poured into ice water (50 mL). The precipitate was collected by filtration to give 3.304 g (97%) of crude 6-bromo-3-(ethyl oxalamido)benzotrifluoride. Crystallization from ethanol/water gave 2.95 g (85%) of pure compound. 1 H NMR (CDCl3): delta1.434 (t, 3H, J=6.9 Hz); 4.432 (q, 2H, J=6.9 Hz), 7.715 (d, 1H, J=8.7 Hz); 7.802 (d, 1H, J=8.7 Hz); 7.946 (d, 1H, J=1.8 Hz), 8.991 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
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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 129316-09-2 as follows. name: 1,3-Dibromo-5-(tert-butyl)benzene

Step 1 1-Bromo-3-(tert-butyl)-5-methoxybenzene (14a) To a solution of 1,3-dibromo-5-tert-butylbenzene (289 mg, 1 mmol) in 20 mL DMF were added NaOMe (2 eq) and Cul (0.03 eq). The mixture was stirred at 80C for 3 h and then was poured into water and extracted with EA. The organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated to give compound 14a as solid (200 mg, 82%).

According to the analysis of related databases, 129316-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); A1;,
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Reference of 21524-34-5, A common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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.

A mixture of 2-bromo-1,3,5-triisopropylbenzene (60.1 mg, 212 mumol), Bu3SnH (68.3 muL, 254 mumol), and V-65 (10.5 mg, 42.3 mumol) in THF-d8 (6 mL) was stirred at reflux for 3 h. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (hexane) to give 2-deutero-1,3,5-triisopropylbenzene (42.9 mg, 98%). 1H NMR (270 MHz): 1.17 and 1.20 (each as s, 18H, CH3), 2.77-2.88 (m, 3H, CH), 6.89 (s, 2.83H, 2-H, 4-H, 6-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:
Article; Mutsumi, Tomonobu; Iwata, Hiroki; Maruhashi, Kazuo; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 67; 6; (2011); p. 1158 – 1165;,
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Electric Literature of 89359-54-6,Some common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, molecular formula is C9H17Br, 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: 4.3.1. ((oct-7-en-1-yloxy)methyl)cyclohexane (H1)To a stirred solution of cyclohexylmethanol (6) (492 muL, 4.0 mmol,2 eq) in DMF (7 mL) under argon was added NaH (60% suspension inmineral oil; 160 mg, 4.0 mmol, 2 eq) at 0 C. The suspension was stirredat 0 C for 30 min, then 8-bromodec-1-octene (7) (336 muL, 2.0 mmol,1 eq) was added dropwise to the mixture. The mixture was allowed towarm to room temperature and stirred for 1 h. After the reaction wasquenched with saturated NH4Cl, the whole was extracted with Et2O.The extract was washed with H2O and brine, then dried over MgSO4.The filtrate was concentrated under reduced pressure to give an oilyresidue, which was purified using silica gel chromatography (petroleum ether_EtOAc=40:1) to afford H1 (341 mg, 76% yield) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 9-Bromo-1-nonene, its application will become more common.

Reference:
Article; Yang, Haoran; Li, Ying; Chai, Huining; Yakura, Takayuki; Liu, Bo; Yao, Qingqiang; Bioorganic Chemistry; vol. 98; (2020);,
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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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-2,4,5-trifluorobenzene

Example 7: Preparation of (R)-benzyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihvdro- ri ,2,41triazolor4,3-aipyrazin-7(8H)-yl)-1 -(2,4,5-trifluorophenyl)butan-2- ylcarbamateA solution of 1 -bromo-2,4,5-trifluorobenzene (638 mg, 3.02 mmol) in THF (5 ml_) was slowly added to a suspension of magnesium turnings (73 mg, 3.02 mmol) in THF (5 ml_). The mixture was allowed to stir for 1 hour at 50 0C. To a solution of (S)-benzyl 1 -iodo-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro- [1 ,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)butan-2-ylcarbamate (406 mg, 0.76 mmol) in THF (5ml_) at -20 0C, cuprous bromide methylsulfide complex (311 mg, 1.51 mmol) was added. The organomagnesium bromide solution was added dropwise and the mixture was allowed to warm up to room temperature. Once de reaction was completed, NH4CI saturated solution (20 ml_) and AcOEt (20 ml_) were added sequentially. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. Digestion in toluene:heptane (5:1 ) leads to the precipitation of (R)-benzyl 4-oxo-4-(3- (trifluoromethyl)-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1 -(2,4,5- trifluorophenyl)butan-2-ylcarbamate (221 mg, 54% yield).

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; ESTEVE QUIMICA, S.A.; BARTRA SANMARTI, Marti; RUSTULLET OLIVER, Albert; FERNANDEZ HERNANDEZ, Sara; MONSALVATJE LLAGOSTERA, Montserrat; WO2010/97420; (2010); A1;,
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Synthetic Route of 876-53-9,Some common heterocyclic compound, 876-53-9, name is 1,3-Dibromoadamantane, molecular formula is C10H14Br2, 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.

Compound 1,3-dibromo-adamantane (3 g, 10 mmol) was dissolved in 30 mL of toluene, and then 250 mg ofAIBN (1.5 mmol), 7 g of tri-n-butyl tin (24 mmol), 3 g of ethyl acrylate (30 mmol) were added in order. The reaction wasrefluxed with at 110 C under nitrogen for 3 hours. The reaction solution was cooled to room temperature and was pouredinto 30 mL of 0.2M aqueous ammonia. After being stirred fully, the organic layer was separated. The aqueous layerswere extracted with ethyl acetate (20 mL34). The organic layers were combined and washed with 30 mL of water and30 mL of saturated sodium chloride solution. The resulting materials were dried with anhydrous sodium sulfate, andsolvent was evaporated under the reduced pressure to give a crude product as a colorless oil, which was separated bysilica column chromatography (petroleum ether : ethyl acetate = 10:1) to give compound NM-011a as a colorless oil (2g, 46.6%). ESI-MS: mlz 337.4 ([M+H]+). 1H-NMR (DMSO-d6, ppm): 1.11 (s, 2 H), 1.15-1.19 (m, 6 H), 1.28-1.39 (m, 12H), 1.53 (s, 2 H), 1.97 (s, 2 H), 2.19-2.24 (m, 2 H), 4.03 (q, 4 H, J=7.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromoadamantane, its application will become more common.

Reference:
Patent; Guangzhou Magpie Pharmaceuticals Co., Ltd.; WANG, Yuqiang; LIU, Zheng; YU, Pei; SUN, Yewei; ZHANG, Zaijun; ZHANG, Gaoxiao; SHAN, Luchen; YI, Peng; LARRICK, James; (27 pag.)EP3150574; (2017); A1;,
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Synthetic Route of 65185-58-2,Some common heterocyclic compound, 65185-58-2, name is 2-Bromophenethylamine, molecular formula is C8H10BrN, 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.

Step A – Preparation of Int Int 59-1 To a stirred solution of 2-bromophenethylamine (20 g, 0.1 mol) in dichloromethane (200 mL ) was added 2,6-lutidine (1 1.8 g, 0.1 1 mol) and 2,2,2-trifluoroacetic anhydride (23.1 g, 0.1 1 mol) at room temperature. The solution was stirred at room temperature for 3 hrs. The solution was washed with IN hydrochloric acid. The organic layer were washed with brine, dried over anhydrous sodium sulfate then filtered. The filtrate was concentrated in vacuum to give the crude product Int 59-1 which was used directly without further purification. MS-ESI (m/z): 295 (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 2-Bromophenethylamine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig, A.; MALETIC, Milana, M.; LUO, Yunfu; QI, Zhiqi; LI, Chun Sing; YU, Tingting; WO2015/73308; (2015); A1;,
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