Tag: M.W=200-300

Synthetic Route 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.

1 , 1-Di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1-ethyl-1 /-/-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 80 (2.50 g, 7.08 mmol) in alpha,alpha,alpha-trifluorotoluene (50 ml). The reaction mixture was heated at 100 C for 1 h. The reaction mixture was allowed to cool to RT then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added dropwise over 15 min. The resultant mixture was heated at 100 C for 45 min. The reaction mixture was cooled to 50 C then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (3.38 ml, 14.15 mmol) was added dropwise over 5 min. The resultant mixture was heated at 100C for 0.5 h then allowed to cool to RT. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The phases were separated then the organic phase was washed with water (2 x 30 ml), saturated aqueous NaHCC solution (20 ml) and brine (10 ml) then dried over Na2S04, filtered and concentrated in vacuo to afford a beige solid (2.5 g). The solid thus obtained was suspended in MeCN (10 ml). The solid was collected by filtration then dried under vacuum to afford the product as an off-white solid (2.30 g, 79%). 1 H NMR (500 MHz, DMSO-cfe) delta 8.07 (s, 1 H), 7.97 (m, 1 H), 7.76 (dd, J = 8.4, 1.5 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.34 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 6.0 Hz, 2H), 4.38 – 4.25 (m, 2H), 1.57 (s, 9H), 1.29 (m, 3H). LC/MS (System A): m/z (ESI+) = 410 [MH+], Rt = 1.17 min, UV purity = 99%.

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; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 143-24-8, name is 2,5,8,11,14-Pentaoxapentadecane, 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 143-24-8, Recommanded Product: 143-24-8

(a) 7-Benzyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]-azepine hydrochloride 10.9 gm (30 mmols) of 1-benzyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine were dissolved in a mixture of 20 ml ethylenediamine and 30 ml tetraethyleneglycol dimethyl ether, and air was passed through the solution at 120 C. for eight hours. Thereafter, the reaction mixture was poured into water, and the aqueous composition was extracted with chloroform. The chloroform extract solution was dried and evaporated, and the residue was chromatographically purified on silicagel with methanol as the mobile phase. Subsequently, the hydrochloride was precipitated from ethanol with ethanolic hydrochloric acid. Yield: 2.4 gm (29% of theory) Melting point: 244-247 C. Calculated: C: 65.33%; H: 6.58%; N: 15.24%; Cl: 12.85% Found: C: 65.01%; H: 6.42%; N: 14.89%; Cl: 12.31%.

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, 2,5,8,11,14-Pentaoxapentadecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4409220; (1983); A;,
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Some common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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: C7H6BrFO

Refined Mg turnings (593 mg, 24.4 mmol) were suspended in dry THF (10 mE). 5-bromo-2-fluoroanisole (1 g, 4.877 mmol) and 1, 2-dibromoethane (500 mg, 2.66 mmol) were dissolved in dry THF (10 mE). The above solution was added to the Mg suspension at room temperature (25 C.) without cooling. After the addition, the reaction was heated to a slight reflux with a heat gun. The reaction was initiated and maintained at reflux for another 0.5 h. An aliquot was quenched with acetone and TEC (petroleum ether) showed most of the starting material was consumed. The mixture of compound E-2 (.-M.244 M in THF) was used in the next step directly.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103291-07-2, its application will become more common.

Reference:
Patent; Pfizer Inc.; Tatlock, John Howard; McAlpine, Indrawan James; Tran-Dube, Michelle Bich; Rui, Eugene Yuanjin; Wythes, Martin James; Kumpf, Robert Arnold; McTigue, Michele Ann; (181 pag.)US2016/244475; (2016); A1;,
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Synthetic Route of 31465-36-8, 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. 31465-36-8 name is 4-(4-Methoxyphenoxy)aniline, 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.

General procedure: To a solution of 3-aminobenzensulfoneamide (2.3g, 13.3 mmol) in DMF (12 ml), K2CO3 (3.8 g, 27.0 mmol)and ethylbromoacetate (2.67 g, 16.0 mmol) were added at ambient temperature. The reaction mixture was stirred for 15 hours atroom temperature. The reaction mixture was quenched with sat. NH4Cland extracted with EtOAc. The combined extracts were washed with brine, driedover MgSO4 and evaporated down. Theresidue was purified by silica gel column chromatography to give 2.44 g ofdesired 2h-1 in 71 % yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-Methoxyphenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Teno, Naoki; Gohda, Keigo; Wanaka, Keiko; Tsuda, Yuko; Sueda, Takuya; Yamashita, Yukiko; Otsubo, Tadamune; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2339 – 2352;,
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Related Products of 36449-75-9, These common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, 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: To a mixture of the benzyl piperidine intermediate 5 (200 mg,0.770 mmol) and potassium carbonate (266 mg, 1.93 mmol) inMeCN (3.0 mL) was added (2-bromoethyl)benzene (137 muL, 1.00 mmol). After reflux for 24 h, EtOAc (9.0 mL) was added to thereaction mixture and the whole was filtered. The filtrate was evaporatedin vacuo and the residue was purified by silica gel chromatographyusing 0-1% MeOH/CHCl3 as eluent to give 228 mg(90%) of the title compound as a pale yellow solid.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshinaga, Hidefumi; Masumoto, Shuji; Koyama, Koji; Kinomura, Naoya; Matsumoto, Yuji; Kato, Taro; Baba, Satoko; Matsumoto, Kenji; Horisawa, Tomoko; Oki, Hitomi; Yabuuchi, Kazuki; Kodo, Toru; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 293 – 304;,
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These common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 C7H6BrFO

(Example 40) 3-{[6-(3-Fluoro-5-methylphenoxy)-1-methyl-1H-benzimidazol-2-yl]methoxy}benzoic acid (Compound No. 1-188) (40a) 1-Fluoro-3-methoxy-5-methylbenzene A mixed solution of 3-bromo-5-fluoroanisole (2.05 g, 10 mmol), trimethylboroxine (50% solution in THF, 2.51 g, 20 mmol), PdCl2(dppf) (0.82 g, 1.0 mmol) and cesium carbonate (6.52 g, 20 mmol) in dioxane (100 mL) and water (50 mL) was stirred with heating under reflux for 10 hours. After leaving to cool, water (100 mL) was added to the reaction solution, followed by extraction with ethyl acetate (200 mL) twice. The organic layers were washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (hexane:ethyl acetate, 6:1) to obtain the title compound (1.40 g, yield: 66%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) delta: 1.78 (3H, s), 6.44 (1H, dd, J = 2.0, 11.0 Hz), 6.50 (1H, d, J = 11.0 Hz), 6.51 (1H, s).

The synthetic route of 1-Bromo-3-fluoro-5-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2138484; (2009); A1;,
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Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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: C10H13BrO

Example 7.9 Preparation of (1S,5R,6R)-3-(3-(benzyloxy)propyl)-10-((3,5-dichlorophenyl)sulfonyl)-5-vinyl-3,10-diazabicyclo[4.3.1]decan-2-one J1 To a solution of (1S,5R,6R)-10-((3,5-dichlorophenyl)sulfonyl)-5-vinyl-3,10 – diazabicyclo [4.3.1] decan-2-one (35.0 mg, 0.0899 mmol) in DMF (1.0 mL) was added NaH (5.39 mg, 0.135 mmol). After 20 minutes ((3-bromopropoxy)methyl)benzene (20.6 mg, 0.0899 mmol) was added, the solution was heated to 80 °C and stirred for 1 h. Et2O (90 mL) was added to the solution and washed with sat. aq. NaCl solution (3 * 10 mL). The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. Column chromatography on SiO2 (Cyclohexane/EtOAc = 1:1) afforded the title compound (31.0 mg, 0.0577 mmol, 64.2 percent) as a colorless solid. Rf: 0.25 (Cyclohexane/EtOAc = 7:3) 1H NMR (600 MHz, CDCl3) delta = 1.28 (s, 2 H), 1.47 – 1.54 (m, 3 H), 1.83 – 1.92 (m, 2 H), 2.23 – 2.29 (m, 1 H), 2.58 – 2.64 (m, 1 H), 2.95 – 3.00 (m, 1 H), 3.49 – 3.59 (m, 4 H), 3.95 – 4.04 (m, 2 H), 4.50 (s, 2 H), 4.65 (d, J = 6.2 Hz, 1 H), 5.09 – 5.15 (m, 2 H), 5.74 – 5.82 (m, 1 H), 7.28 (s, 1 H), 7.33 (d, J = 1.3 Hz, 4 H), 7.56 (s, 1 H), 7.69 (d, J =1.8Hz,2H). 13C NMR (150 MHz, CDCl3) delta = 15.42, 26.29, 26.89, 27.36, 28.14, 29.68, 49.16, 49.53, 51.85, 54.83, 56.84, 67.64, 73.08, 116.8, 124.9, 127.6, 127.7, 128.4, 132.6, 136.3, 137.2, 138.2, 144.1, 169.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54314-84-0, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); A1;,
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Related Products of 24988-36-1, 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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

(B-1) Synthesis of 2,4-bis(2-fluorophenyl)-1,5-dimethoxybenzene 2,4-dibromo-1,5-dimethoxybenzene (88.8g, 300 mmol, 1eq.), 2-fluorophenylboronic acid (100.74g, 720 mmol, 2.4 eq.), Na2CO3 2M aq. (600 mL), Pd(PPh3)4 (6.73g, 6 mmol, 2 mol%), 1,2-dimethoxyethane (150 mL) and toluene (150 mL) were placed in a flask, and the resulting mixture was refluxed for 36 hours. After completion of the reaction, water (500 mL) and toluene (1 L) were added, and the mixture was transferred to a separating funnel, whereby a toluene phase was collected. After drying with MgSO4, original impurities were removed by passing through, a silica gel short column, thereby to concentrate the solution. The thus concentrated solution was recrystallized from a toluene/hexane mixed solvent, whereby white crystals of 86.5g (yield: 88%) of 2,4-bis(2-fluorophenyl)-1,5-dimethoxybenzene were obtained.

The chemical industry reduces the impact on the environment during synthesis 1,5-Dibromo-2,4-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2436679; (2012); 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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1663-61-2

Phenyltriethoxymethane (0.5 mL) and acetic anhydride (0.94 mL) were added to malononitrile (0.17 g), and the mixture was stirred at 140 ° C. overnight.After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure to obtain a crude product.Purification by silica gel column chromatography (ethyl acetate – hexane)2- (Ethoxy (phenyl) methylene) malononitrile(Compound 0022-1, 334 mg) was obtained

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; FUJIFILM CORPORATION; KYOTO UNIVERSITY; KATO, TAKAYUKI; HIRAI, ATSUSHI; MATSUOKA, MASAO; SHIMURA, KAZUYA; (62 pag.)JP6052673; (2016); B2;,
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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. 588-63-6, name is (3-Bromopropoxy)benzene, A new synthetic method of this compound is introduced below., name: (3-Bromopropoxy)benzene

The 148mg Na dissolved in 20ml of absolute ethanol until complete dissolution, 6-benzyl-2-thiouracil200mg (0.92mmol) and 1-(3-bromopropoxy)benzene 297mg (1.38mmol) was added, at room temperature after stirring overnight the reaction was complete by TLC; column chromatography, P:E = 5:1,2:1,1:1, finally give 257 mg of the product, as a white solid, a yield of 79.17percent

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; Peking University; Zhang, Liang; FU, YUHONG; Qin, Hua; Wang, Xiao Wei; Liu, Jun Yi; (30 pag.)CN103864699; (2016); B;,
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