Category: ethers-buliding-blocks

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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Amino-3,3-diethoxypropane

3,3-diethoxypropan-1-amine (1) (5.24 g, 35.6 mmol) was diluted in a mixture of dichloromethane (80 mL) and triethylamine (5.12 mL). The solution was cooled to 0 C., and a solution of di-tert-butyl-dicarbonate (7.85 g, 35.97 mmol) in dichloromethane (20 mL) was slowly added over a 15-minute period. The mixture was stirred for 16 h, at room temperature. The organic phase was washed with 1N HCl (1×100 mL), 0.5N HCl (1×100 mL), and brine (2×100 mL) before it was dried with anhydrous magnesium sulphate, filtered and concentrated. Le crude product was purified by flash chromatography on silica gel (eluent:hexanes/ethyl acetate 7:3). The protected amine was obtained as a yellow oil (8.36 g, 94%). 1H NMR (300 MHz, CDCl3) delta (ppm) 4.93 (s, 1H), 4.53 (t, 1H, J=5.5 Hz), 3.56 (d-quint, 4H, J=38.9 Hz, J=2.3 Hz), 3.20 (q, 2H, J=6.2 Hz), 1.79 (q, 2H, J=6.2 Hz), 1.42 (s, 9H), 1.19 (t, 6H, J=7.1 Hz). 13C NMR (75.5 MHz, CDCl3) delta (ppm) 155.9, 101.9, 78.9. 61.5, 36.7, 33.4, 28.4, 15.3. IR (CHCl3) v (cm-1) 3363 (br), 2979, 2920, 2880, 1708, 1514, 1448, 1393, 1365, 1171, 1139, 1065.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOCPRA SCIENCES SANTE ET HUMAINES S.E.C.; Day, Robert; Neugebauer, Witold A.; Dory, Yves; (40 pag.)US9809621; (2017); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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. HPLC of Formula: C10H12BrFO

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 944317-92-4, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Preparation GW-(2,6-diethylphenyl)-5-[(2E)-3-(dimethyta [(VI) R2 =Me, R3 = CONHR”, R” = 2,6-diethylphenyl]step 5To a solution of 5-acetyl-/V-(2,6-diethylphenyl)-1-methyl-1 H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), A/,A/-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80C for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2S04, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017g, 78% yield).1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1 H), 7.71 (d, J =12.33 Hz, 1 H), 7.36 (s, 1 H), 7.21 (t, J =7.60 Hz, 1 H), 7.12 (d, J =7.60 Hz, 2 H), 5.75 (d, J =12.33 Hz, 1 H), 4.18 (s, 3 H), 3.16 (s, 3 H), 2.92 (s, 3 H), 2.52 (q, J =7.57 Hz, 4 H), 1.09 (t, J =7.57 Hz, 6 H)HRMS (ESI) calcd for C20H27N4O2 [M +H]+ 355.2129, found 355.2133.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; CASUSCELLI, Francesco; BRASCA, Maria Gabriella; CALDARELLI, Marina; CERVI, Giovanni; DISINGRINI, Teresa; QUARTIERI, Francesca; WO2012/139930; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1836-62-0,Some common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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.

EXAMPLE 10a [(1,4-trans)-4-(5-Fluoro-1H-indol-3-yl)-cyclohexylmethyl]-[2-(2 -methoxy-phenoxy)-ethyl]-amine A solution of 4-(5-fluoro-1H-indol-3-yl)cyclohexanecarbaldehyde (0.25 g, 1.02 mmol), 2-(2-methoxy-phenoxy)ethylamine (0.17 g, 1.02 mmol), sodium triacetoxyborohydride (0.32 g, 1.4 mmol) and acetic acid (0.06 ml) in 1,2-dichloroethane (5 ml) was allowed to stir at room temperature for 16 hours. The reaction was quenched with 0.5 N sodium hydroxide (100 ml), extracted with methylene chloride (2 x 100 ml) and washed with brine (2 x 100 ml). The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed under vacuum. Chromatography (2% methanol-ethyl acetate plus 0.2% ammonium hydroxide) afforded 0.1 g (25%) of product. The HCl salt was prepared in ethyl acetate: mp 157-159C.

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

Reference:
Patent; Wyeth; EP1068184; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 38336-04-8

General procedure: Ethyl 2-(4-chloro-3-nitrophenyl)-2-methylpropanoate (3a)(16.15 g, 0.0594 mol), 4 (27.77 g, 0.149 mol), K2CO3 (28.69 g,0.208 mol), KI (0.99 g, 5.94 mmol), TBAB (1.91 g, 5.94 mmol) and150 mL DMSO were added into a round-bottomed flask. The mixturewas heated to 120 C for 24 h then cooling to room temperature.The reaction mixture was diluted with saturated NH4Claqueous solution (250 mL) and extracted with CH2Cl2 (450 mL).The combined organic layer was washed with brine (300 mL), driedover anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by silica gel column chromatography (PE:EtOAc = 4:1) to give compound 5a (15.82 g) as yellow oil in 69%yields.

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; Chen, Dongxing; Shi, Jinyu; Liu, Jing; Zhang, Xueying; Deng, Xiaoying; Yang, Yanyan; Cui, Shuang; Zhu, Qihua; Gong, Guoqing; Xu, Yungen; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 458 – 470;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 104-92-7, 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. 104-92-7, name is 1-Bromo-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of 1.0 mmol of aryl halide in 4 mL of DMF,1.0 mmol of terminal alkyne, 1.5 mmol of piperidine and 0.2 mol%of Pd/Fe3O4NPs were added and the mixture was heated on anoil bath at 110C for 24 h under inert atmosphere (N2). After com-pletion of the reaction (as monitored by TLC), the reaction mixturewas cooled to room temperature and the catalyst was separatedusing a magnetic separator. The solvent was evaporated at reducedpressure, and the residue was subjected to gel permeation chro-matography to afford pure products. All the products are knowncompounds and the spectral data and melting points were identicalto those reported in the literature.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nasrollahzadeh, Mahmoud; Mohammad Sajadi; Rostami-Vartooni, Akbar; Khalaj, Mehdi; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 31 – 39;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 458-50-4, 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 458-50-4 as follows.

At 0 deg.C, 1-bromo-2-fluoro-4-methoxybenzene (5.00 g, 24.39 mmol) in sulfuric acid (20.0 mL) solution was added portionwise potassium nitrate (2.47 g, 24.39 mmol). The reaction mixture was stirred at 0 deg.C for 0.5 h. TLC (petroleum ether: ethyl acetate = 3: 1) indicated the reaction was complete. The reaction mixture was added to ice water (50.0mL) in the quenched (100mL × 2) and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and filtered, and concentrated to dryness under reduced pressure to give the title compound (5.55 g, 90% yield) as a white solid.

According to the analysis of related databases, 458-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 54149-17-6 as follows. Recommanded Product: 54149-17-6

Example 8. 1-{1-[2-(2-ethoxyethoxy)ethyl]piperidin-4-yl}-1W-indazole; To a solution of 1-piperidin-4-yl-1H-indazole TFA salt (0.33 mmol) in DMF (10 ml) was added K2CO3 (137 mg, 0.99 mmol) followed by 1 -bromo-2-(2- ethoxyethoxy)ethane (72 mg, 0.363 mmol). The mixture was heated under N2 atmosphere at 75 “C for 5 hours, cooled down at room temperature and the solvent was evaporated in vacuo. The residue was dissolved in EtOAc (20 ml) and washed with saturated NaHCO3 (10 ml), brine (10 ml) and dried over sodium sulfate to give the crude compound, which was purified by prep LC/MS – high pH (40-70 % acetonitrile/water to give desired compound as free base. The pure compound was dissolved in CH2CI2 (5 ml) under N2 atmosphere and 1 M solution of hydrochloride in Et2O was added (5 eq.). The mixture was stirred at room temperature for 5 minutes and the solvent was evaporated in vacuo to give the desired compound as HCI salt (76 mg, 65.08 %). MS (M+1 ): 318.3; 1 H NMR (400 MHz, METHANOL-D4): delta ppm 1.21 (t, J = 7.03Hz, 3H), 2.28 (d, J = 13.09Hz, 2H), 2.57 (q, J = 13.67Hz, 2H), 3.36 (br t, J = 12.89Hz, 2H), 3.44 (br t, J = 4.69Hz, 2H), 3.57 (q, J = 7.03Hz, 2H), 3.61 – 3.67 (m, 2H), 3.68 – 3.73 (m, 2H), 3.83 (br s, 1 H), 3.85 – 3.90 (m, 7H), 5.00 (tt, J = 11.40, 7.74, 3.91, 3.71 Hz, 1H), 7.14 – 7.21 (m, 1 H), 7.43 (t, J = 7.32Hz, 1H), 7.67 (d, J = 8.59Hz, 1H), 7.75 (d, J = 7.81 Hz, 1H), 8.05 (s, 1 H).

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/142584; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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. COA of Formula: C8H8F3NO

In a round bottom flask fitted with magnetic stirrer and reflux condenser, 3- bromo-4-nitro-pyridine 1 -oxide (5.3 g, 24.25 mmol) and 4-(trifluoromethoxy)benzylamine (9.28 g, 48.55 mmol) were dissolved in propanol (50 ml) and heated to 90 C for 5 hours. Reaction mixture was allowed to cool overnight whilst stirring, with a solid crashing out of the reaction crude. This solid was filtered off, washed with I PA (2 x 10 ml) and dried in vacuo to afford the title compound (4.64 g, 58%). [00294] LCMS Method: 2, RT: 6.50 min, Ml: 330 [M+1] [00295] NMR, Method 1 : (DMSO) 8.82 (t 1 H), 8.05 (d 1 H), 7.94 (d 1 H), 7.52 (d 2H), 7.49 (dd 1 H), 7.36 (d 2H), 4.68 (d 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93919-56-3, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; STOCKLEY, Martin Lee; MACDONALD, Ellen Catherine; PRITOM, Shah; JORDAN, Allan; HITCHIN, James; HAMILTON, Niall; (217 pag.)WO2016/124939; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Bis(2-methoxyethyl)amine

To an ethanolic solution (50 ml) of p-chlorophenol (30 mmol, 3.86 g), bis(2-methoxyethyl)amine (30 mmol, 3.99 g) was added dropwise with constant stirring. After 30 min, 37% (w/v) formalin solution (30 mmol, 2.43ml) was added to it. The resulting mixture was stirred for 1 h at room temperature and then refluxed for 8 h. It was evaporated under reduced pressure and the yellow oil was extracted with saturated brine solution and diethyl-ether several times. The organic phase was separated, dried with anhydrous MgSO4, concentrated by evaporation of ether and subsequently vacuum-dried for the removal of last traces of water.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sanyal, Ria; Chakraborty, Prateeti; Zangrando, Ennio; Das, Debasis; Polyhedron; vol. 97; (2015); p. 55 – 65;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem