Tag: M.W=200-300

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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, This compound has unique chemical properties. The synthetic route is as follows., 701-07-5

EXAMPLE 258A Preparation of 2-iso-propyloxybenzaldehyde The title compound was prepared as in Example 257A but employing 2-iso-propyloxybromobenzene in lieu of 1-bromo-3-isopropoxybenzene. Purification on silica, gel with 10% ether/hexane afforded the title compound (2.3 g, 70%). MS (DCI/NH3) m/z 165 (M+H)+, 182 (M+NH4)+.

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Reference:
Patent; Abbott Laboratories; US6284796; (2001); B1;,
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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. 170015-99-3, name is 2-(4-(Trifluoromethoxy)phenyl)ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 170015-99-3

7-Chloro-5-(pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidine 5k (100 mg, 0.43 mmol) was taken in NMP (4 mL) in a 50 mL round bottom flask under N2. To it was added 2-(4-(trifluoromethoxy)phenyl)ethan-1-amine (107 mg, 0.52 mmol) and the reaction mixture was stirred at rt for 0.5 h. The reaction mixture concentrated in vacuo and the resulting solid taken up in EtOAc and H2O, the organic layer was separated and the aqueous layer extracted with EtOAc (3 * 20 mL). The organic layers combined, washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude was purified by flash chromatography on silica gel (100-200 mesh) using 32% EtOAc-hexane as eluent to afford 59 as a white solid (45 mg, 48%). M.P. 163-165 C. 1H NMR (400 MHz, DMSO-d6): delta 8.74 (d, J = 4.3 Hz, 1H), 8.55 (bs, 1H), 8.54 (s, 1H), 8.45 (d, J = 8.0 Hz, 1H), 8.01 (t, J = 7.6 Hz, 1H), 7.53-7.56 (m, 1H), 7.43 (d, J = 8.5 Hz, 2H), 7.33 (s, 1H), 7.26 (d, J = 7.9 Hz, 2H), 3.75-3.80 (m, 2H), 3.04-3.08 (m, 2H); 13C NMR (100 MHz, DMSO-d6): delta 159.0, 155.5, 154.9, 153.8, 149.2, 148.1, 146.9, 138.3, 137.4, 130.6, 125.2, 121.4, 120.9, 120.0 (q, J = 260 Hz), 84.5, 43.0, 33.5. LCMS (ESI) m/z 401.10.

The synthetic route of 170015-99-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zuniga, Edison S.; Korkegian, Aaron; Mullen, Steven; Hembre, Erik J.; Ornstein, Paul L.; Cortez, Guillermo; Biswas, Kallolmay; Kumar, Naresh; Cramer, Jeffrey; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua; Parish, Tanya; Bioorganic and Medicinal Chemistry; vol. 25; 15; (2017); p. 3922 – 3946;,
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Reference of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
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Application of 4316-51-2, A common heterocyclic compound, 4316-51-2, name is 4-Methoxytriphenylamine, molecular formula is C19H17NO, 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.

Boron tribromide was added to a dichloromethane solution of 4-methoxytriphenylamine (formula (6)) while cooling, and the mixture was stirred at room temperature for 3 hours to obtain diphenylaminophenol (formula (7) in a yield of 90% It was.

The synthetic route of 4316-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YOKOHAMA NATIONAL UNIVERSITY; NAKAGAWA, TETSUYA; YOKOYAMA, YASUSHI; MIYASAKA, YOSUKE; (14 pag.)JP2018/20988; (2018); A;,
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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, Product Details of 29578-39-0

To a solution of 3-bromo-5-fluoroanisole (500 mg, 2.44 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (64 mg, 2.56 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After reaching room temperature, 4-bromobenzaldehyde (542 mg, 2.93 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 used in the next step without further purification. C14H12BrFO2; MW 311.

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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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Synthetic Route of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 35; N-[5-(4-Methyl-piperazin-l-yl)-2-trifluoromethoxy-phenyl]-guanidine; Step 1. 5-(4-Methyl-piperazin-l-yl)-2-trifluoromethoxy-phenylamine; Tris(dibenzilideneacetone)dipalladium, Pd2(dba)3 (1.1 g, 1.2 mmol), 2- dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (0.94 g, 2.4 mmol), 5- bromo-2-trifluoromethoxy-phenylamine (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (IM in THF, 288 mL) and N- methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 h. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved inDCM (200 ml) and washed with water (1 x 100 ml). The organic phases were dried over anhydrous Na2SO4, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 21.1 g of 5-(4-methyl-piperazin- 1 -yl)-2-trifluoromethoxy-phenylamine (64% yield) as a light brown powder.1H NMR (400 MHz, DMSO-J6) delta ppm 2.23 (s, 3 H) 2.42 – 2.47 (m, 4 H) 3.02 – 3.08 (m, 4 H) 5.10 (s, 2 H) 6.16 (dd, J=8.90, 2.93 Hz, 1 H) 6.33 (d, J=2.93 Hz, 1 H) 6.90 (dd, J=8.90, 1.46 Hz, I 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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/74788; (2008); 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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO

General procedure: 4-Bromobenzenamines 1a-c (6.4 mmol) were dissolved in the mixed solvents (2M K2CO3:DMF = 1:1, 24 mL), and then added corresponding 4-substituent phenylboronic acids 2a-h (7.7 mmol) and Pd (PPh3)4 (0.22 mmol) under argon. The reaction mixture was refluxed at 100 for 15 h (TLC monitored the reaction). The reaction was then cooled to room temperature and filtered. The filtrate was added 10 times the amount of water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, concentrated under reduced pressure, and dried to give a crude product. The crude product was purified by flash column chromatography (ethyl acetate/petroleum ether, 1:8-1:5) to afford 1,1′-biphenyl-4-amines 3a-x, yield: 77-95%.

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; Liu, Jingru; Ma, Ruxin; Bi, Fangchao; Zhang, Fa; Hu, Chaoyu; Venter, Henrietta; Semple, Susan J.; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1825 – 1831;,
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Reference of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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 solution of compound 11 (100 mg, 0.21 mmol) and 3-methoxybenzeneboronic acid (49 mg, 0.32 mmol) in dioxane (5 mL) and H2O (0.5 mL) was added Na2CO3 (44 mg, 0.42 mmol) and LiCl (18 mg, 0.42 mmol). Under Ar, Pd(PPh3)4 (24 mg, 0.021 mmol) was added. The mixture was stirred for 12 h at 85C. Water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 67 mg of 12 (yield: 75%) as a colorless liquid.

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-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
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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. 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., 52411-34-4

Then, triphenylphosphine dibromide (0.11 mol) and 150 ml of 1,2-dichloroethane were fed to a reactor equipped with a stirrer, a heater and a dropping funnel in an N2 atmosphere and stirred. A solution obtained by dissolving the intermediate product B (0.05 mol) and triethylamine (0.25 mol) in 50 ml of 1,2-dichloroethane was gradually added dropwise to the resulting mixture at 25 C. After the end of addition, a reaction was carried out at 70 C. for 5 hours. Thereafter, the reaction solution was filtered, and the filtrate was separated with 100 ml of water 5 times. An organic layer was dehydrated with 5 g of sodium sulfate and 1,2-dichloroethane was removed under reduced pressure to obtain an intermediate product C (triphenylphosphine derivative).

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Reference:
Patent; TEIJIN LIMITED; Matsuno, Yuichi; Mitsunaga, Masaki; Oda, Jitsuo; Furuki, Masatsugu; Shoji, Shinichiro; Kitamura, Takuro; Shibata, Yoshitaka; (51 pag.)US9650350; (2017); B2;,
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Electric Literature 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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