Tag: M.W=200-300

Reference 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.

(1) Synthesis of 4,4′-Diformyl-4″-methoxytriphenylamine (8c) Reactions were conducted in the same manner as in (4) in Example 2 except that 20.0 g (0.075 mol) of 4-methoxytriphenylamine (7c) was used in place of triphenylamine (7a). Thus, 19.0 g of 4,4′-diformyl-4″-methoxytriphenylamine (8c) was obtained. Theoretical yield, 76.5%; m.p., 113-114 C. Spectral data for this compound are as follows. 1 H-NMR spectrum (400 MHz, CDCl3, deltappm): 3.85 (3H, s), 6.94 (2H, d, J=9.0 Hz), 7.12 (2H, d, J=9.0 Hz), 7.17 (4H, d, J=8.7 Hz), 7.56 (4H, d, J=8.7 Hz), 9.88 (2H, s)

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; Takasago International Corporation; US5573878; (1996); A;,
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Adding a certain compound to certain chemical reactions, such as: 589-10-6, name is (2-Bromoethoxy)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 589-10-6, name: (2-Bromoethoxy)benzene

Compound 99 (100 mg, 0.371 mmol) to DCM (2 mL) the solution was dissolved in methyl isothiocyanate (30.0 , 0.446 mmol) was slowly added dropwise in a 0 and then, at room temperature two hours then stirred dongan. After checking the completion of the reaction by TLC, the solution was diluted with DCM and extracted with brine. The organic layer was dried over anhydrous Na2SO4, concentrated and filtered. The concentrated filtrate was purified by column chromatography (Hex: EtOAc = 1: 2) to give Compound 101 was synthesized via a (69.3 mg, 55%, colorless oil).

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

Reference:
Patent; Korea Institute of Science and Technology; Ulsan University Academic Cooperation; Kim, Dong Jin; Nam, Gil Soo; Choe, Gyung Ir; Park, Woong Saw; Kim, Young Soo; Pyeon, Sung Lim; Hwang, Hyun Suk; Mun, Doo Hyun; Hwang, Ohn Yu; Sim, Young Sun; Kim, Jin Woo; Kim, Yun Gyung; Kang, Yong Gu; Park, Gi Tuk; (106 pag.)KR101525019; (2015); B1;,
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Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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. name: 1-(Benzyloxy)-3-bromobenzene

Preparation 3 3-Benzyloxyphenyl boronic acid A solution of 3-benzyloxy-bromobenzene 10 g (38 mmol) in 150 mL of anhydrous THF was cooled to -70C under a nitrogen atmosphere. 28.5 mL of n-butyl lithium (1.6 M in hexanes) was added dropwise to the solution. The reaction mixture was stirred for 30 minutes, then tri-isopropyl borate 10.6 mL (45.6 mmol) was added. The reaction mixture was allowed to warm to ambient temperature over a two hour period. The reaction was quenched by the addition of 200 mL of 1 N HCl andthe reaction mixture was stirred for an additional hour. The slurry was extracted twice with EtOAc and the organic layer separated and combined. The EtOAc solution was washed twice with brine, dried with Na2SO4, and evaporated to a yellow oil. The product was crystallized from ether-hexane. This yielded 4.85 g of the title compound as white solid. PMR: Consistent with the proposed structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53087-13-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; EP838461; (1998); A2;,
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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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrO2

To a mixture ofl-bromo-2,4-dimethoxybenzene (72 jiL, 0.50 mmol, 1 equiv), cyclopropylboronic acid (64 mg, 0.75 mmol, 1.5 equiv), and K3PO4H2O (0.35 mg, 1.5 mmol, 3 equiv) was added toluene (400 iL) then a THF stock solution of 3 and PAd3 (100 iL, 0.25 iimol of Pd/PAd3) and the mixture was stirred at 100 C for 5 h. The reaction mixture was diluted withethyl acetate then extracted with water. The combine organic layers were evaporated and the crude product was purified by flash chromatography. After drying, 80 mg (90 %) of 23 was obtained as a colorless oil. NMR spectroscopic data agreed with literature values.

According to the analysis of related databases, 17715-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE TRUSTEES OF PRINCETON UNIVERSITY; CARROW, Brad P.; CHEN, Liye; (51 pag.)WO2017/75581; (2017); A1;,
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Reference of 175278-17-8, A common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: Tert-butyl (R)-(5-(trimethylsilyl)pent-4-yn-2-yl)carbamate (160 mg, 0.63 mmol) was added in DMF (2.5 mL) to a sealed vial containing amino-halide (0.5 mmol), sodium carbonate (106 mg, 1.00 mmol), lithium chloride (21.00 mg, 0.50 mmol) and Pd(dppf)Cl2.CH2Cl2 (14.62 mg, 0.02 mmol). The reaction was degassed for 10 min, then heated to 100 C for 4 hours. After cooling, the reaction was diluted with EtOAc and washed with water and brine. The organic was dried over Na2SO4 and evaporated, then the crude product was purified by flash silica chromatography (EtOAc / heptane). Pure fractions were evaporated to dryness to afford the indole.

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moss, Thomas A.; Lister, Andrew S.; Wang, Jimmy; Tetrahedron Letters; vol. 58; 32; (2017); p. 3136 – 3138;,
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Application of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Tert-butyl 2-acetyl-3 – ((tert-butyldimethylsilyl) oxy) -5- (methoxymethyloxy) -6- (pivaloyloxy) benzoate (5.00 g, 9.79 mmol, 1 eq) 0 g), and the temperature was raised to 85 C. Subsequently, N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added thereto, followed by stirring at 85 C. After stirring for 2.5 hours, it was cooled to room temperature and concentrated under reduced pressure to remove half of the solvent amount (25.0 g). The same amount of toluene as the distilled solvent was added and heated again to 85 C. Then N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added and the mixture was incubated for 2 hours did. The reaction solution was concentrated under reduced pressure until the solvent disappeared, toluene was added to this concentrated solution, the total amount was adjusted to be 20 times by weight of the product on the assumption that the yield was 100%. Iodine (2.02 g, 7.96 mmol, 3 eq) and pyridine (0.21 g, 2.65 mmol, 1 eq) were added to 30.0 g of the adjusted solution (estimated to contain 1.50 g of enamine compound, 2.65 mmol) C. for 2 hours. Acetic acid (0.30 mL, 5.30 mmol, 2 eq) was added after confirming the disappearance of the raw material by HPLC analysis, and after reacting at 50 C. for 3 hours and 30 minutes, 15% aqueous sodium thiosulfate solution (26.7 g) Was added and stirred, and the organic phase was taken out. The organic phase was washed with water (7.5 g) and concentrated under reduced pressure. Toluene was added to the obtained crude product, and the total amount was adjusted to 5.2 g. Heptane (7.0 g) was added to the solution, and the mixture was cooled to 5 C. and recrystallized to obtain tert-butyl 3-iodo-7- (methoxymethyloxy) -4-oxo-6- (pivaloyloxy) -4H- Chromene-5-carboxylate as a white solid (yield 72.3%).

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

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; Tanaka, Yui; Fujiwara, Yuji; (25 pag.)JP2015/113324; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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 35822-58-3, Formula: C11H15BrO2

To a solution of aryl bromide (1.94 g, 7.49 mmol, 1.0 equiv) in THF (20 mL) at -78 C under N2 was added 1.5 M n-BuLi in hexanes (7.49 mL, 11.2 mmol, 1.5 equiv). After 30 mm DMF (869 iL, 11.2 mmol, 1.5 equiv) was added. The mixture was slowly warmed to r.t. over 4 h, at which time it was quenched with sat. aq. NH4C1 (40 mL) and extracted with EtOAc (3 x 20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. The resultant oil was purified by flash chromatography on silica gel (95:4:1 hexanes/EtOAc/Et3N) to yield the product (2.105 g, 87%) as a yellow oil. R1= 0.46 (3:1 hexanes/EtOAc). The analytical data match those previously reported: Ueda, M.; Kawai, S.; Hayashi, M.; Naito, T.; Miyata., 0. 1 Org. Chem. 2010, 75, 914.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; SALK INSTITUTE FOR BIOLOGICAL STUDIES; PACHE, Lars; CHANDA, Sumit, K.; VAMOS, Mitchell, Dennis; COSFORD, Nicholas David, Peter; TERIETE, Peter; MARLETT, John; DIAZ, Arturo; YOUNG, John, A.T.; WO2015/187998; (2015); A2;,
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Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)methyl)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 54314-84-0, COA of Formula: C10H13BrO

(Step 3) {1-[1-(1-Tert-butyloxycarbonyl)piperidin-4-yl] imidazolidin-2-ylidene}malononitrile (3.68 g, 11.59 mmol) obtained in the Step 2 was dissolved in DMF (25 mL) and the solution was added with potassium carbonate (3.20 g, 23.18 mmol) and benzyl-3-bromopropylether (2.46 mL, 13.91 mmol), followed by stirring at 80°C for 6.5 hours. Further, the mixture was added with potassium carbonate (1.60 g, 11.59 mmol) and benzyl-3-bromopropylether (1.72 mL, 5.80 mmol), followed by stirring at 80°C for 14.5 hours. The mixture was added with saturated brine and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol (20:1)) to obtain {3-(3-benzyloxypropyl)-1-[1-(1-tert-butyloxycarbonyl)piperidin-4-yl]imidazolidin-2-ylidene} malononitrile (4.84 g, 89.6 percent) as a white solid. 1H NMR (CDCl3, deltappm): 1.45 (s, 9H), 1.49-1.56 (m, 2H), 1.74-1.79 (m, 2H), 1.94-2.04 (m, 2H), 2.81 (brt, J = 12.3 Hz, 2H), 3.38-3.45 (m, 2H), 3.52-3.60 (m, 4H), 3.69 (t, J = 7.1 Hz, 2H), 4.18-4.35 (m, 3H), 4.49 (s, 2H), 7.26-7.38 (m, 5H).

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-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1847530; (2007); A1;,
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These common heterocyclic compound, 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, 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. name: 4-(Benzyloxy)aniline hydrochloride

A solution of Ethyl 2-Acetyl-4- (2, 4-dichlorophenyl)-4-oxobutanoate from Exl, Step A (2.85 g, 9.0 mmol) and 4-benzyloxyaniline hydrochloride (2.14 g, 9.1 mmol) in 1: 1 ethanol/acetic acid (80 mL) was heated at reflux for 18h. After cooling, the solution was partially concentrated and diluted with ethyl acetate. It was washed with saturated NaHC03 solution, and the organic layer was dried (MgS04) and concentrated. The residue was purified by flash column chromatography (10: 1 hexanes/EtOAc) to afford the title compound as a white solid (1.67 g, 39%) :’H NMR (300 MHz, CDC13) 8 6.90-7. 40 (m, 12H), 6.73 (s, 1H), 5.02 (s, 2H), 4.31 (q, J= 7.1 Hz, 2H), 2.40 (s, 3H), 1.36 (t, J= 7.1 Hz); ESI MS m/z 480 [C27H23Cl2NO3 + H] + ; HPLC (Method A) 99.6% (AUC), {R = 36.2 min.

The synthetic route of 4-(Benzyloxy)aniline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/80328; (2005); A1;,
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Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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. Product Details of 19056-40-7

To a solution of 4-bromo-3-(methoxymethyl)aniline (0.6 g, 2.78 mmol) andpotassium phosphate tribasic (0.295 g, 1.39 mmol) in acetonitrile (25 mL) at 0 °C, was added 2,4-dibromobutyryl chloride (0.88 g, 3.33 mmol) dropwise. The reaction mixturewas warmed to rt and stirred for 1 h. NaOH (0.6 g, 15.0 mmol) (in 1.2 mL water, 50percentaqueous solution) was added to the reaction mixture, which was stirred at rt for 3 h. The reaction mixture was filtered, the solid was rinsed with acetonitrile, and the filtrate was concentrated. The crude product was purified by flash chromatography (eluting with 20- 30percent EtOAc in hexane) to give 3-bromo-1-(4-bromo-3-(methoxymethyl)phenyl)pyrrolidin-2-one (0.71 g, 70percent yield) as a pale brown oil. MS(ESI) m/z: 363.8 (M+H) ?HNMR (300 MHz, chloroform-d) oe ppm 7.69 – 7.64 (m, 1 H), 7.63 – 7.60 (m, 1 H), 7.57 -7.53 (m, 1 H), 4.59 (dd, J6.8, 3.0 Hz, 1 H), 4.52 (s, 2 H), 4.12 -4.01 (m, 1 H), 3.90 -3.79 (m, 1 H), 3.50 (s, 3 H), 2.80 – 2.67 (m, 1 H), 2.55 – 2.41 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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