Author: Jessica.F

366-99-4, A common compound: 366-99-4, name is 3-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 4; Parallel Synthetic Method B, for Library II Compounds; Fifty mL (13.5 mmol) of the prepared (4,6-dichloro-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl) amine solution was divided equally (2 mL or 0.54 mmol each) among 25 barcoded, 40 mL scintillation vials. Individual solutions of each R2NHR (where R2 amine indicates Monomer 2 in Table 2, 0.542 mmol) and DIEA (77 mg /104 muL, 0.596 mmol) in 0.5 mL of CH3CN were prepared and added to the correspondingly labeled 40 mL vials. The resulting solutions were shaken on the J-KEM block overnight at room temperature and then placed in a freezer (about -14 ¡ã C.) without purification until the next reaction.; Example 5; Parallel Synthetic Method C, for Library III Compounds; In an oven-dried round bottom flask, a solution of cyanuric chloride (5.0 g, 27.1 mmol) in 1,4-dioxane (40 mL) was cooled to freezing in a CH3CN/dry ice bath. To this frozen solution was added 40 mL of CH3CN, followed by DIEA (3.85 g/5.19 mL, 29.8 mmol). A solution of 3-fluoro-p-anisidine (3.83 g, 27.1 mmol) in 10 mL of CH3CN was then added slowly via syringe. The reaction mixture was stirred at about -20¡ã C. for about 1h and allowed to warm to room temperature over 1 h. The resulting 2-amino-4,6-dichlorotriazine solution was carried to the next step without purification.

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-Fluoro-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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Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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. 35896-58-3

Compound 3 (0.32 g, 1.5 mmol) was dissolved in acetonitrile (2 mL), and an excess of asolution of K2S2O8 (1.6 g, 6 mmol) in 3mL water was added at 25 C. The reactionmixture was stirred at room temperature for 1 h. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was extracted withdichloromethane (10mL 3). The organic layers were washed with brine until neutrality,then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude productwas purified by a silica-gel column chromatography with petroleum ether and EtOAc(3:1) to give CoQ0, 0.26 g, 96%, red needles, m.p 56-57 C (lit5 57-59 C). IR: (cm1)3590, 3415, 1661, 1603, 1291, 1226, 999. 1H NMR (400 MHz, CDCl3) d 6.44 (q,J1.7 Hz, 1H), 4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J1.6 Hz, 3H,CH3). 13C NMR (101 MHz, CDCl3) d 184.4 (C5O), 184.2(C5O), 145.0, 144.8, 144.0,131.2, 61.2 (OCH3), 61.1 (OCH3), 15.4 (CH3). GC-MS (EI): m/z 182. The spectroscopicdata are in accord with the literature

The chemical industry reduces the impact on the environment during synthesis 1,2,3,4-Tetramethoxy-5-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qiu, Yong-Fu; Yan, Yi-Yu; Lu, Bin; Tang, Lei; Zhai, Yu-Lin; Chen, Ke-Xin; Wang, Jin; Organic Preparations and Procedures International; vol. 51; 6; (2019); p. 602 – 605;,
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A common compound: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 60792-79-2

[0329] In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min. A solution containing Boc20 (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2C12 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2- aminoethoxy)ethylcarbamate (850 mg, 74%).

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, 60792-79-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; BEMIS, Jean E.; VU, Chi B.; MILNE, Jill C.; JIROUSEK, Michael R.; DONOVAN, Joanne; WO2014/107730; (2014); A2;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 103291-07-2

Under a nitrogen atmosphere, 4-fluoro-3-methoxybromobenzene (163 mg) was added dropwise to a THF suspension of magnesium (23 mg) and iodine (catalytic amount). After heating under reflux,After stirring at room temperature for 30 minutes, {(5S) -2-oxo-5- (propan-2-yl) -3- [6- (trifluoromethyl) pyridin-3-yl] imidazolidin-1-yl} acetaldehyde A THF solution of (50 mg) was added dropwise. After stirring at room temperature for 2 hours,A saturated ammonium chloride aqueous solution was added, and the mixture was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by preparative HPLC.DMSO (2 mL) of the obtained product2-iodoxybenzoic acid (27 mg) was added to the solution,Stir overnight at room temperature. After adding water and filtering through Celite,The filtrate was extracted with chloroform. After concentrating the organic layer under reduced pressure,The residue was purified by PTLC (silica gel, hexane / ethyl acetate = 1: 1),The title compound (24 mg) was obtained.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co Ltd; Moriya, Minoru; Yamamoto, Shuji; Abe, Kimiyoshi; Ota, Hiroyuki; Sun, Ziang Min; Wakasugi, Daisuke; Araki, Hiroko; (49 pag.)JP2015/157764; (2015); A;,
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Adding some certain compound to certain chemical reactions, such as: 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, 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 3401-47-6. 3401-47-6

2-Methoxynaphthalene-1-thiol (compound 11r) was prepared as follows. (Preparation of (2-methoxynaphthalen-1-yl)magnesium bromide) A THF solution (8 mL) of 1-bromo-2-methoxynaphtalene (4 g, 16.87 mmol) was added, dropwise, to a THF slurry (17 mL) of magnesium turnings (533 g, 21.93 mmol) that had been previously activated through the addition of 1,2-dibromoethane (150 muL, 1.69 mmol). The flask was gently heated with a heat gun, while avoiding boiling. After 30 min, the flask was irradiated at rt in an ultrasonic cleaning bath for 2.5 h to afford a THF solution of the Grignard reagent. Elemental sulfur (0.757 g, 23.62 mmol) was added in one portion, under a N2 blanket, to the 0 C. solution of (2-methoxynaphtalen-1-yl)magnesium bromide (vide supra). After 30 min, lithium aluminum hydride powder (0.32 g, 8.44 mmol) was added in very small portions. After 30 min, the reaction was diluted with cold, aqueous, saturated NH4Cl (20 mL) and then aqueous citric acid 2M (5 mL). The mixture was extracted with dichloromethane (3¡Á30 mL) and, after the removal of volatiles, the resulting slightly yellow solid was partially dissolved with pentane. The pentane solution was cooled by immersion into a -78 C. cooling bath and after 5 min the temperature was raised to 0 C. After 15 min the solution was filtered to afford 3.01 g (94%) of compound 11r as a white crystalline solid: Mp 66-67 C. (lit. 65-68 C.). 1H NMR (400 MHz, Chloroform-d) delta 7.98 (dd, J=8.5, 0.9 Hz, 1H), 7.74 (d, J=8.2 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 7.49 (ddd, J=8.4, 6.8, 1.3 Hz, 1H), 7.34 (ddd, J=8.0, 6.8, 1.1 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 4.39 (s, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, Chloroform-d) delta 151.51, 132.01, 129.28, 128.43, 126.64, 126.28, 124.04, 123.98, 114.72, 112.71, 56.82; IR (ATR) 3052, 2937, 2838, 2579, 1506, 1265, 1247, 1075, 797, 767, 741 cm-1; HRMS calculated for C22H18O2S2 (disulfide) 401.0640. found 401.0648 (M+Na)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Bromo-2-methoxynaphthalene.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY GHOST; FLEMING, FRASER FERGUSSON; Lujan-Montelongo, Jesus Armando; US2015/239833; (2015); A1;,
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929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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 1 moles of a double-terminal amine polyether (structure of formula (2), R 2 = R 3 = H, n = 3), 18 moles of dichloroethane and 1 mole of sodium hydroxide (an aqueous solution having a concentration of 20% by weight) were charged into a reaction flask equipped with a cooling apparatus, 4 C, then slowly add 1 mole of acryloyl chloride, the temperature of the addition process does not exceed 15 C, after the addition of acryloyl chloride, the reaction is carried out at 15 C for 3 hours; the resulting reaction is allowed to stand and the organic phase is separated, Washed with saturated aqueous NaCl solution 3 times, dried with anhydrous sodium sulfate, the organic solvent was distilled off to obtain a crude product of orange-red viscous liquid, and the crude product was washed with acetone to obtain the product of polymerization grade. The product of the polymerization stage was confirmed to be a monomer represented by the formula (1) (wherein Ri = R2 = R3 = H, n= 3) using an infrared spectrum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; CHINA PETROLEUM & CHEMICAL CORPORATION;.; DRILLINGRESEARCH INSTITUTE OF SINOPEC ZHONGYUAN PETROLEUM ENGINEERING CO., LTD; WANG, ZHONGHUA; (12 pag.)CN104926678; (2017); B;,
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2674-34-2, These common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, 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.

To a solution of A (146 g, 50 mmol) in 250 ml of THF was slowly added n-butyllithium (50 mL, 2.5 M/L in hexane) at -78 C under argon. The mixture was kept at -78 for 1 hour. Then, pinacol borate (25.3 g, 100 mmol) was added, followed by slowly warming to room temperature, and the mixture was stirred overnight. The mixture was extracted twice with diethyl ether and washed with distilled water and brine. Further purification by silica gel column chromatography using hexane as eluent.A white solid (15 g, yield 80%), i.e., 2,5-dimethoxy-1,4-diborate benzene (B), was obtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2674-34-2.

Reference:
Patent; Chinese Academy Of Sciences Chemical Institute; Li Xiaojun; Li Yongfang; Pan Fei; Zhang Zhiguo; (21 pag.)CN109748925; (2019); A;,
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321-28-8, A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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: To a solution of the selected anisole or biphenyl (13.0mmol) in 30mL of dry CH2Cl2 at 0 C, p-toluoylchloride (2g, 13.0mmol), and AlCl3 (3g, 22.05mmol) were added and the mixture was stirred at rt overnight. After addition of ice, the mixture was diluted with CH2Cl2, washed with NaHCO3 saturated solution, dried and evaporated to dryness.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gobbi, Silvia; Hu, Qingzhong; Foschi, Giacomo; Catanzaro, Elena; Belluti, Federica; Rampa, Angela; Fimognari, Carmela; Hartmann, Rolf W.; Bisi, Alessandra; Bioorganic Chemistry; vol. 86; (2019); p. 401 – 409;,
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929-75-9, 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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 3-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-4-methyl-2H-chromen-2-one (19, 200 mg, 0.268 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 52 mg, 0.27 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (119 mg, 0.268 mmol), and the mixture was stirred at the same temperature for 2 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (20:1) to give the desired product 21c (84 mg, 34%). Mp 307.4+/-0.2 C; 1H NMR (500 MHz, DMF-d7): delta=8.93 (s, 1H), 8.06 (br t, J=5.8 Hz, 1H), 7.97 (s, 2H), 7.87 (s, 1H), 4.75 (t, J=7.0 Hz, 2H), 3.80 (t, J=5.8 Hz, 2H), 3.69 (s, 2H), 3.65-3.70 (m, 2H), 3.62-3.65 (m, 4H), 3.57-3.60 (m, 4H), 3.36 (q, J=5.8 Hz, 2H), 3.31 (t, J=5.8 Hz, 2H), 2.51 (s, 3H), 2.44-2.57 (m, 2H), 2.32-2.39 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=169.3, 161.2, 152.9, 149.2, 145.7, 134.2, 126.3, 122.9, 121.3, 120.8, 120.0, 112.4, 70.24, 70.16, 70.09, 70.07, 69.5, 67.1, 49.0, 39.9, 39.3, 27.7, 21.4, 14.9 ppm; IR (ATR, neat): nu=2927, 1703 (CO), 1654 (CO), 1614, 1561, 1200, 1146, 1113, 835 cm-1; MS (ESI): m/z: 920 [M+H+]; HRMS (EI): m/z calcd for C33H34F17N5O6: 919.2238 [M+]; [M+] not found.

The synthetic route of 1,11-Diamino-3,6,9-trioxaundecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
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Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. 2674-34-2

K2CO3 (1.13g, 8.19mmol), boronate ester 17 (800mg, 1.78mmol), and dibromoarene 11 (176mg, 0.593mmol) in toluene (20mL), EtOH (4mL) and H2O (2mL) was sparged with Ar for 1h. Pd(PPh3)4 (73mg, 0.063mmol) was added, the mixture was sparged with Ar for an additional 20min, and then heated 90C for 16h. The reaction mixture was cooled to rt and diluted with 50mL of H2O. The reaction mixture was extracted with Et2O (3¡Á50mL). The combined organics were washed with 150mL of brine, dried with Na2SO4, and the solvents were removed under vacuum. The product was isolated via column chromatography as a white solid (433mg, 99%), mp 248-250C. 1H NMR (CDCl3): delta 8.09 (d, J=1.8Hz, 2H), 7.80 (dd, J=8.0, 1.8Hz, 2H), 7.53 (d, J=8.0Hz, 2H), 7.49 (s, 6H), 6.91 (s, 2H), 3.76 (s, 12H), 1.41 (s, 36H). 13C NMR (CDCl3): delta 169.0, 151.3, 150.3, 141.6, 136.8, 132.2, 131.6, 130.3, 129.9, 128.4, 121.8, 121.7, 112.8, 56.0, 51.8, 35.0, 31.5. FTIR (cm-1): 1720.79. UV-vis (CH2Cl2) lowest E abs lambdamax [nm] ( [M-1cm-1]): 337 (22,801). Em. (CH2Cl2) lambdamax [nm]: 424. Anal. Calcd for C52H62O6: C, 79.76; H, 7.98. Found: C, 77.41; H, 8.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2674-34-2, its application will become more common.

Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
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