Ethers-buliding-blocks

Reference of 36865-41-5, 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 36865-41-5 as follows.

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine.To a suspension of Mg (911 mg, 37.5 mmol) and iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of l-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard- formation started. The rest of the l-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard-sol. (IM in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4- dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 0C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane – > EtO Ac/heptane 1 :1) yielded the title compound (1.51 g, 62%). LC-MS: tR = 0.80 min; ES+: 260.15.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
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Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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. category: ethers-buliding-blocks

A 250 mL round-bottomed flask was charged with 5-bromo-2-methoxy-phenol ( 1 .5 g, 76.4 mmol), l -bromo-3-methoxy-propane (12.9 g, 84 mmol), K >C( , (22 g, 2 153 mmol) and DM F (50 mL). The resultant mixture was stirred at 50 C for 3 hours, and then ethyl acetate and water was added. The organic phase was separated, and then dried over anhydrous Na?SO.and then concentrated to give 4-bromo- l -methoxy-2-(3-methoxypropoxy)benzene (23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; YANG, Song; HAN, Xingchun; WANG, Zhanguo; (96 pag.)WO2015/173164; (2015); A1;,
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Synthetic Route of 39538-68-6, The chemical industry reduces the impact on the environment during synthesis 39538-68-6, name is 2-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

Iron (5.35 g, 95.7 mmol) was added to a solution of 2-nitro-5-methylanisole (10, 4.00 g, 23.9 mmol) in ethanol (60 ml) and 6 M aqueous hydrochloric acid (30 ml), and the mixture was heated at reflux for 2 h. The reaction mixture was diluted with ethyl acetate and filtrated through Celite. Evaporation of the filtrate afforded crude 11. NaNO2 (2.11 g, 30.6 mmol) was added to a solution of crude 11 (2.80 g, 20.4 mmol) in THF (80 ml) and 4 M aqueous hydrochloric acid (40 ml) at 0 C. After 30 min, potassium iodide (4.80 g, 30.6 mmol) was added, and the mixture was heated at reflux for 3 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate and brine, dried with sodium sulfate, and evaporated. Purification by silica gel column chromatography (n-hexane/ether 100:1 to 98:2) gave 12 (pale yellow oil, 3.77 g, 15.2 mmol, 65% for two steps). 1H NMR (500 MHz, CDCl3) delta 7.60 (d, 1H, J=7.9 Hz), 6.63 (d, 1H, J=1.2 Hz), 6.53 (dd, 1H, J=7.9, 1.2 Hz), 3.84 (s, 3H), 2.31 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 157.84, 139.86, 138.96, 123.36, 112.07, 81.78, 56.18, 21.42; HRMS (FAB+) m/z 248.9780 [(M+H)+: calcd for C8H10OI, 248.9776].

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Iwashita, Masazumi; Fujii, Shinya; Ito, Shigeru; Hirano, Tomoya; Kagechika, Hiroyuki; Tetrahedron; vol. 67; 33; (2011); p. 6073 – 6082;,
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Application of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15-9: Preparation of 2-(4-methyl-2-nitro-phenyl)-thiazole (65).; The procedure described in Example 15-1 was followed except that 4-methyl-2-nitro- thiobenzamide (56) was used instead of 4-trifluoromethyl-2-nitro-thiobenzamide, bromoacetaldehyde-dimethylacetal was used instead of 1 -bromo-3-methyl-butan-2-one, and the reaction was acid catalyst with 5% acetic acid. This gave the title compound (66 mg, 75%). LC/MS: (Method I): tR= 0.98 min, >90%, m/z (ESI+)= 221 (MH+).

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

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14922; (2007); A1;,
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Reference of 62415-74-1,Some common heterocyclic compound, 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, molecular formula is C7H6Br2O, 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.

Synthesis of Intermediate I-1 (0258) 5.31 g (20.0 mmol) of 1,2-dibromo-4-methoxybenzene, 3.30 g (30.0 mmol) of pyrocatechol, 0.190 g (1.0 mmol) of CuI, 0.264 g (1.0 mmol) of 18-crown-6, and 8.28 g (60.0 mmol) of K2CO3 were dissolved in 150 mL of dimethylformamide (DMF), and stirred at a temperature of about 140 C. for about 24 hours. The solution was cooled to room temperature, 60 mL of water was added thereto, and an organic layer was extracted three times therefrom using 60 mL of diethyl ether. The obtained organic layer was dried using magnesium sulfate (MgSO4), and the MgSO4 was removed by filtration. A solvent was next removed therefrom by evaporation. The obtained residue was separated and purified through silica gel chromatography to produce 3.21 g of Intermediate I-1 (yield: 75%). The obtained compound was identified by liquid chromatography-mass spectrometry (LC-MS). C13H10O3: M+1 215.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4-methoxybenzene, its application will become more common.

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Youngkook; Jung, Hyejin; Han, Sanghyun; Hwang, Seokhwan; (115 pag.)US2017/77419; (2017); A1;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: (4-(Trifluoromethoxy)phenyl)methanamine

6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one To a suspension of 6-((6-chloropyridazin-3-yl)oxy)quinolin-2(1H)-one (0.032 g, 0.117 mmol) in dioxane (2.0 mL) at room temperature was added 4-(trifluoromethoxy)benzylamine (0.091 mL, 0.585 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (3.28 mg, 5.85 mumol), palladium (II) acetate (1.313 mg, 5.85 mumol) and sodium-t-butoxide (0.014 mL, 0.164 mmol). The reaction mixture was stirred in a sealed tube at 110 C. overnight, then concentrated under vacuum to a yellow oil. This was purified by prep HPLC to yield 6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one as a white solid (4 mg, 5%). 1H NMR (500 MHz, METHANOL-d4) delta ppm 7.96 (d, J=9.5 Hz, 2H), 7.67-7.34 (m, 8H), 6.68 (d, J=9.6 Hz, 1H), 4.59 (s, 2H). LCMS: R.T.=1.738 min; [M+H]+=429.08.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
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These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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. Formula: C9H13NO2

To a solution of (S)-2-((4-(benzyloxy)phenoxy)methyl)oxirane(1.0 g, 3.9mmol) in iPrOH (40 ml), was added 2-(2-methoxyphenoxy)ethanamine (0.98 g,5.8mmol) in iPrOH dropwise under 50C for 5h. The reaction mixture was cooled to roomtemperature, and removed the solution, water was added, extracted with EA. The organic layerwas washed with water, brine, dried over Na2SO4, concentrated under reduced pressure andpurified by silica column, to give (S)-1-(4-(benzyloxy)phenoxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol (0.52 g, 1.228mmol).

The synthetic route of 2-(2-Methoxyphenoxy)ethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Bitna; Jahangir, Alam; Evans, Andrew K.; Briggs, Denise; Ravina, Kristine; Ernest, Jacqueline; Farimani, Amir B.; Sun, Wenchao; Rajadas, Jayakumar; Green, Michael; Feinberg, Evan N.; Pande, Vijay S.; Shamloo, Mehrdad; PLoS ONE; vol. 12; 7; (2017);,
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These common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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: 1-(2-Methoxyphenyl)-N-methylmethanamine

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

The synthetic route of 1-(2-Methoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
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Synthetic Route of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-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.

General procedure: A solution of 6.00 g (22.8 mmol) of 1,2-dibromo-4,5-dimethylbenzene in 12 mL of tetrahydrofuran wasadded to preliminary prepared 30 mL of a 1M solutionof iso-PrMgLiCl in tetrahydrofuran and stirred at -17to -13C. After 3 h, 5.12 g (23.25 mmol) of chlorodiphenylphosphinewas added dropwise to the solutionat -20 to -10C. The obtained solution was stirred for30 min at -10C, and then it was allowed to warm upto room temperature, stirred for additional 16 h, andevaporated. 30 mL of methylene chloride and 20 mLof a saturated aqueous solution of ammonium chloridewere added to the residue. The organic phase wasseparated and dried over anhydrous sodium sulfate.The residue after the evaporation was recrystallizedusing an ethanol-acetone mixture.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
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Reference of 109-85-3,Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, 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 2,3-dichloro-1,4-naphthoquinone (0.341g, 1.50mmol) in 1.5mlof ethanol was added 2-methoxyethylamine (0.124g, 1.65mmol) and triethylamine (0.227g,2.25mmol) and the mixture stirred at r. t. for 18h. The red precipitate formedwas filtered under suction, washed with distilled water and dried to afford (4) as a dark red solid, 87.8%.1H (CDCl3) delta 8.15 (dd, 1H, J=0.94, 7.68Hz), 8.03 (dd, 1H, J=0.99, 7.67Hz), 7.72 (dt, 1H, J=1.31, 7.59Hz), 7.62 (dt, 1H, J=1.28, 7.55Hz), 6.36 (br s, 1H), 4.06(dd, 2H, J=5.60, 10.62Hz), 3.63(t, 2H, J=5.17Hz), 3.42 (s, 3H); 13C(CDCl3) delta 180.42, 176.84, 144.37, 134.85, 132.67, 132.44, 129.88,126.80, 77.20, 71.22, 58.95, 44.50.

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

Reference:
Article; Ho, Si-Han Sherman; Sim, Mei-Yi; Yee, Wei-Loong Sherman; Yang, Tianming; Yuen, Shyi-Peng John; Go, Mei-Lin; European Journal of Medicinal Chemistry; vol. 104; (2015); p. 42 – 56;,
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