Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 19056-41-8, name is 3-Bromo-4-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 19056-41-8, COA of Formula: C7H8BrNO

To cyanuric chloride (0.184 g, 1.0 mmol) dissolved in acetonitrile (3 mL) stirring at about -10 C., was added a solution of 3-bromo-p-anisidine (0.2019 g, 1.0 mmol) in acetonitrile followed by the addition of N,N-diisopropylethylamine (DIEA) (0.17 mL, 1.0 mmol) in acetonitrile. The reaction mixture was allowed to stir at about -10 C. for 1 hour under nitrogen. The reaction mixture was then warmed to room temperature and allowed to stir at room temperature for another hour under nitrogen. To the reaction mixture was added a solution of cycloheptylamine (0.13 mL, 1.0 mmol) in acetonitrile followed by addition of DIEA (0.17 mL, 1.0 mmol). The reaction mixture was allowed to stir at reflux overnight under nitrogen. To the reaction mixture was added N-methyl-4(methylamino)piperidine (0.13 mL, 1.0 mmol) in acetonitrile followed by the addition of DIEA (0.17 mL, 1.0 mmol). The reaction mixture was allowed to stir at reflux for overnight under nitrogen. The reaction mixture was extracted 3 times with ethyl acetate; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on the rotary evaporator and the resulting solid was dried overnight under vacuum. Column chromatography (silica gel, 90:9:1 methylene chloride:methanol:conc. ammonium hydroxide yielded 0.029 g (6%)of 123. 1H NMR (400 MHz, CDCl3) delta 7.97-8.19 (broad resonance, 1H), 7.12 (broad resonance, 1H), 6.78-6.80(m, 2H), 4.82 (br s, 1H), 4.58 (br s, 1H), 3.92 (br s, 1H), 3.84 (s, 3H), 2.90-2.98 (m, 5H), 2.29 (s, 3H), 2.17 (broad resonance, 2H), 1.99-2.24 (broad resonance, 4H), 1.72-1.85 (m, 3H), 1.42-1.62 (m, 11H); MS (ESI): m/z 520 (100), 518 (93.9), 458 (10.4), 424 (20.8), 422 (21.1), 261 (67.5), 260 (63.4), 213 (13.9), 212 (13.6).

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, 3-Bromo-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
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Related Products of 35822-58-3, A common heterocyclic compound, 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, molecular formula is C11H15BrO2, 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.

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

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; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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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. Recommanded Product: 1-Bromo-4-cyclopropoxybenzene

A mixture of intermediate compound 11 (2.34 mmol, 0.5 g), potassium phthalimide (2.81 mmol, 0.52 g) and copper (I) iodide (2.81 mmol, 0.54 g) in dimethylacetamide (6 mL) was refluxed under argon for 18 h. After cooling to room temperature, the reaction mixture was treated with 2N potassium hydroxide (5 mL), and partitioned with EtOAc (25 mL) and saturated 2N potassium hydroxide (25 mL). The organic layer was separated and washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated to afford 547 mg of the title compound which was precipitated in acetonitrile. The solid was filtered and washed with hexane, dried over vacuum to afford 221 mg of the pure title compound (221 mg, Yield: 34%). 1 H NMR (400 MHz, CDCI3) delta 7.98-7.95 (2H, m), 7.80-7.78 (2H, m), 7.36-7.32 (2H, m), 7.20-7.16 (2H, m), 3.80-3.75 (1 H, m), 0.82-0.81 (4H, m) LC-MS: tR= 3.55 [M+H]+ not ion (method 3).

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

Reference:
Patent; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; GARCIA GARCIA, Francisco, Javier; SALAS SOLANA, Jordi; WO2013/149996; (2013); A1;,
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2357-52-0, name is 4-Bromo-2-fluoroanisole, 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. COA of Formula: C7H6BrFO

A mixture of 4-Bromo-2-fluoro-1-methoxybenzene (107 g, 0.5244 mol, from step (ii) above ), CuCN (70.4 g, 0.7866 mol) in dry DMF (150 ml) was stirred at 120 C overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. Organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel using 3% ethyl acetate in petroleum ether gave the sub-title compound (24.4 g) as a solid.

The synthetic route of 2357-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/123748; (2005); A1;,
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Application 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.

General procedure: To an oven-dried 5 mL screw-capped vial, in a glove box 2-methyl-N-(8-quinolinyl)benzamide (79 mg, 0.3 mmol), 1-bromobutane (82 mg, 0.6 mmol), Ni(OTf)2 (10.6 mg, 0.03 mmol), PPh3 (15.6 mg, 0.06 mmol), Na2CO3 (64 mg, 0.6 mmol) and toluene (1 mL) were added. The mixture was stirred for 24 h at 140 °C followed by cooling. The resulting mixture was filtered through a celite pad and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc= 20/1) to afford the desired alkylated product (84 mg, 88percent) as a colorless oil.

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:
Article; Aihara, Yoshinori; Wuelbern, Jendrik; Chatani, Naoto; Bulletin of the Chemical Society of Japan; vol. 88; 3; (2015); p. 438 – 446;,
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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. 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 873980-68-8

Preparation 40: 2-methoxy-5-methyl-4-(1 -methyl-1 A7-pyrazol-4-yl)aniline To a solution of 4-bromo-2-methoxy-5-methylaniline (Preparation 39, 350 mg, 1 .620 mmol) in EtOH (2.5 mL), toluene (2.5 mL) and water (2.5 mL) was added 1 -methylpyrazole-4- boronic acid pinacol ester (404 mg, 1 .944 mmol), sodium carbonate (343 mg, 3.24 mmol) and Pd(PPh3)4 (225 mg, 0.194 mmol). The reaction mixture was heated to 80C for 2.5 hours, under nitrogen. The reaction mixture was cooled to room temperature and diluted with EtOAc (30 mL), washed with water (30 mL) and brine (30 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-5% MeOH in DCM to give the title compound (140 mg, 36%). 1 H NMR (500 MHz, CDCI3): delta 7.56 (d, J = 0.5 Hz, 1 H), 7.39 (s, 1 H), 6.75 (s, 1 H), 6.63 (s, 1 H), 3.96 (s, 3H), 3.86 (s, 3H), 3.76 (br s, 2H), 2.27 (s, 3H). LCMS (ESI) Rt = 1 .13 minutes MS m/z 218.30 [M+H]+

The synthetic route of 873980-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; SOLANKI, Savade; WOODWARD, Hannah; NAUD, Sebastian; BAVETSIAS, Vassilios; SHELDRAKE, Peter; INNOCENTI, Paolo; CHEUNG, Jack; ATRASH, Butrus; WO2014/37750; (2014); 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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

A solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), methanesulfonylacetic acid (2.35 g, 17.0 mmol) and HBTU (6.89 g, 18.2 mmol) in DMF (70 mL) was stirred at ambient temperature one minute. DIEA (6.5 mL, 37.2 mmol) was added all at once, and the resultant solution was stirred at ambient temperature. The solution was poured into water, and the product crystallized. The product, 5.4 g (99%), was collected by filtration and was used without any further purification in the subsequent reaction. MS m/z 320 (MH+). 1H NMR(DMSO-d6) delta 3.17 (s, 3H), 4.25 (s, 2H), 5.07 (s, 2H), 7.00 (d, 2H), 7.32-7.55 (m, 7H) and 10.32 (s, 1H).

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; Carson, John R.; McNally, James J.; US2005/182108; (2005); A1;,
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Reference of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: Preparation of (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

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; Ty, Nancy; Pontikis, Renee; Chabot, Guy G.; Devillers, Emmanuelle; Quentin, Lionel; Bourg, Stephane; Florent, Jean-Claude; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1357 – 1366;,
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Synthetic Route of 112970-44-2, 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. 112970-44-2 name is 2-Bromo-3-methoxyaniline, 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.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)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 60876-70-2, Quality Control of 1-Bromo-4-(tert-butoxy)benzene

Synthesis of (4-tert-butoxy-phenylethynylVtrimethyl-silane (2). A 20 mL microwave tube was charged with a mixture of 1 -bromo-4-tert- butoxybenzene 1 (1.0 g, 4.36 mmol), PdCl2(dppf) (71 mg, 0.087 mmol), CuI (33 mg,0.174 mmol), DIPA (0.924 mL, 6.55 mmol), and THF (15 mL). Tube was backfilled with nitrogen, sealed, and irradiated in a microwave reactor (max. power 250W) at 100C for 5 min. Solution was diluted with water (200 mL) and extracted with EtOAc (3 x 80 mL). Combined organic layers were washed with water (1 x 100 mL) and brine (1 x 80 mL), dried (Na2SO4), filtered and concentrated in vacuo. Crude product was purified by normal phase flash chromatography (40 g SiO2, 0-30% EtO Ac/Hex) to provide the desired compound 2 (488 mg, 45%) as a clear colorless oil. LC-MS: [M+H]+= Not observed; Ret. Time (Method A) 7.87 min; 1H NMR (250 MHz, CDCl3) delta 0.2 (s, 9H), 1.3 (s, 9H), 6.9 (d, 2H), 7.4 (d, 2H).

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-4-(tert-butoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHAOGEN, INC.; WO2008/154642; (2008); A2;,
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