Tag: M.W=200-300

Electric Literature of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000849j To a stirred solution of compound 3 (1 g, 1 eq) in POC13 (2 mL), cyclopropane carboxylic acid (0.5 mL) were added. The resulting reaction mixture was heated at 120 C for 3h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 X 20 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. LCMS (mlz): 250.95 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
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1435-51-4, 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 1435-51-4 as follows.

step 1-A solution of 57a, sodium methoxide (1 equivalent) and DMF were stirred overnight under an N2 atmosphere at RT. The volatile solvents were removed in vacuo and the residue partitioned between Et2O and water. The organic phase was washed with 5% NaOH, water and brine, dried (MgSO4), filtered and evaporated to afford 57b.

According to the analysis of related databases, 1,3-Dibromo-5-fluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
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Reference of 90562-10-0, A common heterocyclic compound, 90562-10-0, name is 1-Bromo-4-(3-bromopropyl)benzene, molecular formula is C9H10Br2, 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.

The starting material was prepared using an analogous procedure to that described in Example 35 for the preparation of 3-(4-allyloxyphenyl)-1-methoxypropane but starting from 3-(4-bromophenyl)propyl bromide. There was thus obtained 3-(4-bromophenyl)-1-(methoxy)propane; NMR (CDCl3): 1.8-2.0(2H, m), 2.6-2.7(2H, t), 3.3-3.4(5H, m), 7.0-7.1(2H, d) and 7.3-7.4(2H, d).

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US5919793; (1999); A;,
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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. 51554-93-9, name is 1-Bromo-4-octylbenzene, A new synthetic method of this compound is introduced below., Product Details of 51554-93-9

Synthesis compound CM8a pursuant method of the International Publication No. 2012/086671.er the nitrogen gas ambient in the reaction vessel, was added 4-bromo – n – octyl benzene (250g) and tetrahydrofuran (dehydrated product, 2.5L) or less, cooled to -70 . Thereto was added dropwise 2.5 mole / L concentration of n – butyllithium – hexane solution (355 mL), to -70 stirred for 3 hours or less time. Then, after which the dropwise dissolved in tetrahydrofuran (dehydrated product, 400mL) in a compound CM8a (148g) added, warmed to room temperature and stirred at room temperature overnight. After the reaction mixture obtained was cooled to 0 , water (150 mL) with stirring. The obtained reaction mixture was concentrated under reduced pressure to remove the organic solvent. In the reaction mixture obtained was added hexanes (1L) and water (200 mL), separating operation to remove the aqueous layer. After the organic layer with water, washed with saturated brine obtained, dried over magnesium sulfate. The obtained mixture was filtered and the filtrate obtained was concentrated under reduced pressure to give a yellow oil of compound CM8b (330g).

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; SUMITOMO CHEMICAL COMPANY, LIMITED; YOSHIDA, SADAMU; KAKIMOTO, HIDENOBU; (125 pag.)TW2016/9758; (2016); A;,
Bromide – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, I believe this compound will play a more active role in future production and life. 156682-52-9

To a solution of (S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.7 mmol) in 1,4-dioxane (15 mL) at rt, were added 1,4-dibromo-2,3-difluorobenzene (2.4 g, 8.7 mmol), K3PO4 (3.7 g, 17 mmol) and, N,N-dimethylethylenediamine (0.15 g, 1.7 mmol). The reaction mixture was purged with nitrogen for 5 min and then charged with copper (I) iodide (0.17 g, 0.87 mmol). The reaction mixture was again purged with nitrogen for 3 min and heated at 95 C. for 12 h. The reaction mixture was cooled, filtered through a Celite pad and the filtrate was concentrated under reduced pressure. The crude compound was purified by column chromatography (3% MeOH-CHCl3) to yield Intermediate 28 (0.80 g, 2.6 mmol, 30% yield) as a yellowish solid. MS(ESI) m/z: 305.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta=7.59 (ddd, J=8.8, 7.0, 2.3 Hz, 1H), 7.24 (ddd, J=9.0, 7.0, 2.0 Hz, 1H), 4.80 (t, J=5.0 Hz, 1H), 4.20-4.04 (m, 1H), 3.37 (dd, J=5.0, 4.0 Hz, 2H), 2.56-2.45 (m, 1H), 2.43-2.35 (m, 1H), 2.25-2.18 (m, 1H), 2.07-1.95 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 156682-52-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Shirude, Pravin Sudhakar; Baligar, Vishweshwaraiah; Seshadri, Balaji; Chattopadhyay, Amit Kumar; Wurtz, Nicholas R.; Kick, Ellen K.; (91 pag.)US2019/270704; (2019); A1;,
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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. 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H12BrN

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

According to the analysis of related databases, 6274-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
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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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (4-Bromo-2-fluorophenyl)methanamine

Step c) 2-[(4-Bromo-2-fluorophenyl)methyl]-1,2,3,4-tetrahydro-1,3-dioxo-4-isoquinolinecarboxylic Acid Methyl Ester To a solution of 3-methoxyl-1-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester (5.0 g, 21.37 mmol) in DMF (100 mL) were added 4-bromo-2-fluorobenzylamine (4.36 g, 21.37 mmol) and Et3 N (5.96 mL, 42.74 mmol). The mixture was stirred at 80 C. for 30 minutes, poured into H2 O (1500 mL), acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/hexane (after cooling to -20 C.) gave a white solid (7.6 g, 87.7%, m.p. 149-150 C.). 1 H NMR (DMSO-d6, 400 MHz): delta [3.67 (s), 4.0 (s), 3H, –CO2 Me, tautomeric], [5.06 (q), J=15.4 Hz, 5.30 (s), 2H, –NCH2 –, tautomeric], 5.4 (s), 1H, CH–CO2 Me, tautomeric], 7.07-8.43 (m, 7H, Ar–H, tautomeric). IR (KBr, cm-1): 1670 (CO), 1605 (CO). MS (+FAB): 406 (80, M+ +H), 374 (40, M+ –OCH3). Anal. Calcd.: C, 53.22; H, 3.23; N, 3.45. Found: C, 53.19; H, 2.98; N, 3.4.

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; American Home Products Corporation; US5068332; (1991); A;,
Bromide – Wikipedia,
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Electric Literature of 875664-41-8, 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. 875664-41-8 name is 3-Bromo-4,5-difluoroaniline, 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.

1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid (200 mg, 0.73 mmol) was dissolved in N,N-dimethylformamide (2 mL). HATU (0.35 g, 0.91 mmol) was added followed by diisopropylethylamine (0.38 mL, 2.19 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Then, 4-fluoro-3,5-dimethylaniline (0.2 g, 1.46 mmol) was added. The resulting mixture was stirred for 24 hours and next poured onto 10 mL of ice. The mixture was extracted using 2-Me-THF (3 x 10 mL). The combined organics were washed withbrine, dried on Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55C for24 hours yielding compound 80 (130 mg):Compound 100 to 105 were prepared similarly as described for compound 80, using 1-methyl-4-[[(1 S)-2,2,2-trifluoro- 1 -methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid instead of 1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid and the corresponding aniline instead of 4-fluoro-3 ,5 -dimethylaniline. After addition of the aniline, the mixture was stirred at 50C forhours instead of 24 hours at room temperature.Crude compound 100 was purified by silica gel chromatography heptane-EtOAc 100/0 to 0/100. The product was crystallized from diisopropylether (15 mL)/iPrOH (3.5 mL). The product wasfiltered off, washed with diisopropylether (3x), and dried at 50C in vacuo, resulting in compound 100 (251 mg). MethodA; Rt: 1.98 mi mlz: 489.8 (M-H) Exactmass: 491.0. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.08 (d, J=6.8 Hz, 3 H), 3.84 – 4.00 (m, 4 H), 7.36 (d, J=2.0Hz, 1 H), 7.66 (d, J=1.8 Hz, 1 H), 7.80 – 7.93 (m, 2 H), 8.20 (br. s., 1 H), 10.31 (br. s., 1 H).?9FNMR (377 MHz, DMSO-d6) oe ppm -138.51 –138.34 (m, 1 F), -133.99 –133.81 (m, 1 F), -76.07 (d, J=7.9 Hz, 3 F). Differential scanning calorimetry: From 30 to 300 C at 10C/mm:peak at 199.0 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4,5-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Bromide – Wikipedia,
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Application of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-bromo-3-(tertbutyl)benzene (300 mg, 1.41 mmol) was dissolved in dry THF (5 mL) at -78 C under nitrogen and was stirred for 10 min. n-BuLi (2.5 M in hexanes, 2.0 mL, 4.9 mmol) was added drop wiseto the solution was stirred for 2 h at -78 C. After two hours, ethyl fluoroacetate (0.16 mL, 1.69mmol) was added drop wise and stirred for 1 min at -78 C upon which the mixture was then quenched with NH4Cl (20 mL) and warmed to room temp. The mixture was then extracted withether (50 mL), and dried over MgSO4. After concentration in vacuo (note: remove shortly afterthe ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (hexane: ethyl acetate = 90:10) to yield the product as a yellowliquid in 43percent yield (0.12 g).

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
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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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2-fluorobenzotrifluoride

0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl were added to 11 ml of toluene solution containing 1 g of the free form of the compound (F) obtained above and 0.73 g of 4-bromo-2-fluorobenzotrifluoride and the entire mixture was refluxed overnight under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the target compound. Viscous oil 1H-NMR(CDCl3, deltappm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q, 2H), 3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H), 7.16(d, 1H), 7.38(t, 1H)

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIPPON SODA CO., LTD.; HAMAMOTO, Isami; TAKAHASHI, Jun; YANO, Makio; KAWAGUCHI, Masahiro; HANAI, Daisuke; IWASA, Takao; EP1932844; (2015); B1;,
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