Category: ethers-buliding-blocks

Related Products of 1000574-79-7, A common heterocyclic compound, 1000574-79-7, name is 2-Bromo-4-(difluoromethoxy)aniline, molecular formula is C7H6BrF2NO, 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.

(25a) N-[2-Bromo-4-(difluoromethoxy)phenyl]formamide Into acetonitrile (80 mL), 2-bromo-4-(difluoromethoxy)aniline (4.40 g, 18.5 mmol) and formic acid (1.1 mL, 27.5 mmol) were dissolved, to which 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (7.7 g, 28 mmol) and 4-methylmorpholine (3 mL, 27 mmol) were added, followed by stirring at room temperature for six hours. Ethyl acetate and water were added for extraction, and the resulting organic layer was sequentially washed with water and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 – 60 : 40, V/V) to give the desired title compound (4.1 g, yield 83%). 1H-NMR (CDCl3) 5: 6.47 (1H, t, J = 73.0 Hz), 7.13 (1H, dd, J = 9.1, 2.6 Hz), 7.39 (1H, d, J = 2.6 Hz), 7.58 (1H, br s), 8.41 (1H, d, J = 9.1 Hz), 8.49 (1H, s).

The synthetic route of 1000574-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; AOKI, Kazumasa; MATSUI, Satoshi; YOSHIKAWA, Kenji; SHIMIZU,Hiroki; SASAKI, Junko; NAKAJIMA, Katsuyoshi; KANNO, Osamu; OIZUMI, Kiyoshi; EP2565185; (2013); 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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine, A new synthetic method of this compound is introduced below., SDS of cas: 131713-50-3

Step 1 A solution of Cbz-D-Valine (500 g, 1.99 mol) and N-methylmorpholine (201.8 g, 1.99 mol) in anhydrous THF (8 L) was cooled to -15 C., i-butylchlorofomate (299 g, 2.19 mol) was added dropwise under stirring. After 30 min, a solution of 1-amino-2,2-dimethoxypropane (209.5 g, 1.99 mol) in THF (1 L) was added slowly and the temperature was maintained at -15 C. for 2 h. The reaction mixture was washed with brine (2 L) and the organic phase was concentrated to remove the THF. The residue was diluted with EtOAc (4 L), washed with 1N aqueous HCl (2*2 L), washed with sat. NaHCO3 (2 L) and Na2CO3 (2 L), and washed with brine (1.5 L). After drying over Na2SO4, the organic solvent was removed under reduce pressure to afford (R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate as a white solid (670 g, yield 99.5%), which was used for next step without further purification. LC-MS m/z 360.9 [M+Na]+. 1H NMR (CD3OD 300 MHz): delta 7.35-7.30 (m, 5H), 5.08 (s, 2H), 4.45-4.35 (m, 1H), 3.95-3.85 (m, 1H), 3.34-3.25 (m, 8H), 2.10-1.90 (m, 1H), 0.94-0.91 (m, 6H).

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; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
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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 33839-11-1 as follows. category: ethers-buliding-blocks

3-EthyI-4-methoxyphenylboronic acid 6. To a stirred solution of 4-bromo-2-ethyl-l-methoxybenzene (4.59 g, 21 mmol) in dry THF (50 mL)5 cooled to -78C5 was added slowly drop-wise (over 45 min) n-BuLi (15 mL of a 1.6 M solution in hexanes, 24 mmol). The solution was stirred at -78C for 2 h before trimethylborate (3.6 mL, 31.5 mmol) was added drop-wise and the reaction was allowed to warm slowly to rt with stirring overnight. The reaction was quenched with 2M HCl (50 mL) and the products extracted with EtOAc (2 x 50 mL). These extracts were combined and concentrated under reduced pressure to give an oily substance. To this was added hexane followed by a small amount of DCM and the resulting white precipitate was collected by filtration and washed with hexane. Yield 1.55 g, 41%: 1H NMR delta (270 MHz, CDCl3) 1.27 (3H, t, J= 7.5 Hz)5 2.73 (2H5 q, J = 7.5 Hz)5 3.90 (3H5 s), 6.60 (-1H5 bs), 6.96 (IH5 d, J = 8.4 Hz)5 7.98 (IH5 d5 J = 1.5 Hz)5 8.08 (IH5 dd, J = 8.2, 1.7 Hz); LC/MS (APCI) m/z 179.04 (M-H)”; HPLC ttau = 2.1 min (>99%) 90% MeCN in H2O.

According to the analysis of related databases, 33839-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); 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. 1187160-18-4, name is 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

Step A: Rac-7-methoxy-indan-1-ylamine hydrochloride (2.20 g, 0.01 1 mmol) was dissolved in acetic acid (100 mL). After cooling to 0 C. sulfuryl chloride (1.88 mL, 0.23 mmol) was slowly added and the reaction mixture was stirred for 16 h at ambient temperature. Then the solvent was evaporated and the residue was taken up in isopropanol. Thereby a precipitate formed which was isolated and dried on high vacuum to yield rac-4,6-dichloro-7-methoxy-indan-1-ylamine (2.0 g, 68%) as a white solid; MS: m/e=269.6 (M+H+).

The synthetic route of 1187160-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kolczewski, Sabine; Riemer, Claus; Roche, Olivier; Steward, Lucinda; Wichmann, Juergen; Woltering, Thomas; US2009/227570; (2009); A1;,
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Reference of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to -30 C and “Buli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at -30 C followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eg). The reaction was stirred and warmed to RT over 30 min. The volatiles were removed under N2 purge and the residue was redissolved in 3:1 THF/NMP (11 mL). The MOM-protected bromophenol (2.2 mmol, 1.0 eg) and Pd(PtBu3)2 (22 mg, 44 mumol, 4 mol %) were added and the reaction was heated to 100 C for 2 h. The reaction was cooled to RT and the THF was removed. The residue was diluted with CH2C12, washed with 1 M HCI, and dried over Na2S04. The crude material was purified by flash chromatography. Synthesized by General Method Cl. Purified by flash chromatography (Biotage FLASH 40S KP-Sil silica, 0-5% EtzO/hexanes) to yield 0.59 g (84%) of 31 as a white solid. ?H NMR (CDCl3,300 MHz): 8.48 (s, 1H), 8.03 (d, J= 8.7 Hz, 2H), 7.65 (dd, J= 8.7 Hz, J = 0.6 Hz, 2H), 7.50-7.20 (m, 6H), 7.09 (d, J= 1.8 Hz, 1H), 4.84 (s, 2H), 3.00 (s, 3H), 2.38 (s, 3H).

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-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYMYX TECNOLOGIES, INC; WO2005/108406; (2005); A1;,
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These common heterocyclic compound, 127657-97-0, name is Benzyloxyacetaldehyde dimethyl acetal, 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. Computed Properties of C11H16O3

L-Ascorbic acid (44.9 g, 0.255 mol) was added to a solution of compound Tr-1 (60 g, 0.306 mol) in dry acetonitrile (898 mL) followed by addition of pTSA monohydrate (15.5 g, 0.076 mol) and the reaction mixture was heated at 90 C for 1 h. After completion of the reaction (TLC), half the volume of the acetonitrile was distilled off and the process was repeated twice. Solvent was removed completely and the title compound as a mixture of stereoisomers was obtained (91 g). The product was directly taken to the next step without further purification.

The synthetic route of Benzyloxyacetaldehyde dimethyl acetal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; BETHEL, Richard; ENEROTH, Anders; KLASSON, Bjoern; OeBERG, Fredrik; (73 pag.)WO2016/30335; (2016); 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. 4457-67-4, name is 1-Bromo-4-methoxybutane, A new synthetic method of this compound is introduced below., Formula: C5H11BrO

EXAMPLE 10 10-Hydroxy-10-(4-methoxybutyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole Ether (60 ml) and 4-bromo-1-methoxy-butane (10.2 g) were added to magnesium turnings (1.46 g). After formation of the Grignard reagent, the mixture was cooled to 0¡ã and 3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.72 g) in dry 1,2-dichloroethane (20 ml) added dropwise over 20 minutes. The solution was stirred under argon at 0¡ã C. for 1 hour, poured onto a swirling mixture of ice (100 ml) and saturated aqueous ammonium chloride (60 ml) and the mixture was stirred for a further 20 minutes. The mixture was concentrated in vacuo and the aqueous residue extracted with chloroform (3*100 ml). The extracts were dried (Na2 SO4) and concentrated in vacuo. Ether (20 ml) was added and the product was filtered and recrystallized from ethyl acetate to give the title compound or the free base (3.55 g), m.p. 128¡ã-139¡ã C. The free base was acidified with ethereal HCl to give the title compound as the hydrochloride, m.p. 178¡ã-179¡ã C. Found: C, 61.55; H, 7.55; N, 8.80percent C16 H22 N2 O2.HCl requires: C, 61.85; H, 7.45; N, 9.0percent.

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; John Wyeth & Brother Ltd.; US4784996; (1988); 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. 31963-35-6, name is 1-(2-Phenoxyphenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(2-Phenoxyphenyl)methanamine hydrochloride

Example 95: 4-Chloro-6-(2-phenoxy-benzyIamino)-2H-phthalazin-l-one; A mixture 6-bromo-4-chloro-2H-phthalazin-l-one (150 mg, 0.58 mmol), 2- phenoxy-benzylamine hydrochloride (151 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 8O0C for Ih. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2-phenoxy-benzylamino)-2H-phthalazin-l-one: 81 mg (37.0%): m/z (M+eta)=378. 1H-NMR (DMSO-J5) delta: 12.77 (s,lH), 8.34 (d,lH), 8.03(m,lH), 7.82 (m,3H), 7.71 (m,lH), 7.56 (m,3H), 7.42 (m,2H), 7.33 (dd,lH), 7.20 (s,lH), 4.84 (d,2H).

The synthetic route of 31963-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
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Synthetic Route of 2186-92-7,Some common heterocyclic compound, 2186-92-7, name is P-anisaldehyde dimethyl acetal, molecular formula is C10H14O3, 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: Under an atmosphere of argon, to a mixture of benzaldehyde dimethyl acetal (0.152 g, 1.0 mmol) and Al-MCM-41 (30 mg, Si/Al=48, dried prior to use at 120 C for 1 h under vacuum) in dichloromethane (1.5 mL), allyltrimethylsilane (0.172 g, 1.5 mmol) in dichloromethane (0.5 mL) was added through a syringe at 30 C. The reaction mixture was stirred at 30 C for 45 min. The catalyst was removed by filtration and washed with dichloromethane (40 mL). After the filtrate was concentrated under reduced pressure, almost pure homoallyl methyl ether was obtained. Further purification by silica-gel column chromatography (hexane to hexane/Et2O=10:1) afforded 4-methoxy-4-phenylbut-1-ene[27] and 27(a) as a colorless oil (0.151 g, 93%).

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

Reference:
Article; Ito, Suguru; Hayashi, Akira; Komai, Hirotomo; Yamaguchi, Hitoshi; Kubota, Yoshihiro; Asami, Masatoshi; Tetrahedron; vol. 67; 11; (2011); p. 2081 – 2089;,
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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. 57602-02-5, name is 1,14-Dibromo-3,6,9,12-tetraoxatetradecane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 57602-02-5

Example 2 Synthesis of Double End-Substituted Pentaethyleneglycol-Sumatriptan (SMQT-02) Sumatriptan (236 mg, 0.8 mmol) is dissolved in 2 mL dry DMF, 60% NaH (32 mg, 0.8 mmol) is added, stirred and react 15 minutes, triethylene glycol 2-bromoethyl (145.6 mg, 0.4 mmol) is added, and reaction is performed overnight under nitrogen gas protection. Water is added to the above reaction liquid to quench the reaction, extraction is performed three times by using acetic ether, an organic phase is dried by using anhydrous sodium sulfate, concentrate goes through column separation to obtain 184 mg product, with a yield rate 58%. 1H-NMR (CDCl3): 2.34 (s, 12H), 2.70 (t, 4H), 2.72 (s, 6H), 2.94 (t, 4H), 3.06 (t, 4H), 3.40 (t, 4H), 3.49 (s, 12H), 4.35 (s, 4H), 6.98 (s, 2H), 7.11 (d, 2H), 7.23 (d, 2H), 7.60 (s, 2H), 8.91 (s, 2H).

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 57602-02-5.

Reference:
Patent; JENKEM TECHNOLOGY CO.,LTD.(TIANJIN); XU, Lihua; ZHAO, Xuan; FENG, Zewang; WANG, Jinliang; WANG, Zhenguo; (16 pag.)US2016/82117; (2016); A1;,
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