Author: Jessica.F

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. HPLC of Formula: C11H25NO2

Step (2): synthesis of 4-formyl-benzoic acid tert-butyl ester:; 4-Formylbenzoic acid was suspended in 60 mL of benzene, and the mixture was placed under a nitrogen atmosphere. The mixture was brought to reflux and N,N -dimethylformamide di-tert-butylacetal was added dropwise via an addition funnel over 45 minutes. The yellowish suspension gradually turned golden yellow and became a homogeneous solution. The solution was refluxed an additional 60 minutes before stirring overnight at room temperature. The resulting orange solution was diluted to about 100 mL with ethyl acetate (“EtOAc”), and the resulting solution was washed sequentially with water, saturated sodium bicarbonate (2 x 100 mL), and brine (100 mL). The solvent was removed by rotary evaporation. The resulting amber oil was injected on to a BIOTAGE Flash 65i (350 g, silica gel) cartridge and purified with a 30-minute gradient of from 5% to 25% v/v EtOAc in heptane. Product fractions were pooled, and the solvent was rotary evaporated. The resulting golden oil was dried under house high vacuum overnight at room temperature to give 3.92 g (57% yield) of 4- formyl-benzoic acid tert-butyl ester as a yellow solid; IH NMR (400 MHz, DMSO-D6) delta ppm 1.54 (s, 9 H) 8.00 (dm, /=8.30, Hz, 2 H) 8.07 (dm, /=8.30, 2 H) 10.08 (s, 1 H); Mass Spectrum MH” 206.

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/61715; (2006); A2;,
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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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-(difluoromethoxy)benzene

Example 178 2-[5-[4-(Difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide To a solution of the compound synthesised in Reference Example 36 (50.0 mg, 122 mumol), 1-bromo-4-(difluoromethoxy)benzene (20.1 muL, 147 mumol) and tetrakistriphenylphosphine palladium (7.08 mg, 6.12 mumol) in 1,4-dioxane (2.0 mL) is added a solution of potassium carbonate (50.8 mg, 367 mumol) in water (0.40 mL), and the mixture is stirred under reflux for 2 hours. After the reaction, the reaction mixture is poured into water at 0C, and extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The drying agent is removed by filtration, and the solvent is evaporated under reduced pressure. The obtained crude product is purified by silica gel chromatography (hexane/ethyl acetate = 3/1) to give 2-[5-[4-(difluoromethoxy)phenyl]-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide (21.1 mg, 41 %). IR (cm-1): 696, 1111, 1495, 1674, 1774

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1719761; (2006); 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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C18H21NO4

General procedure: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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Electric Literature of 116557-46-1, 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. 116557-46-1, name is 3-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3 A solution of 3-bromo-2-methoxyaniline from Step 2 (1.94 g, 9.60 mmol), 4,4,445,5,55′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (3.66 g, 14.40 mmol), PdCl2(dppf)-CH2Cl2 complex (0.392 g, 0.480 mmol) and potassium acetate (2.83 g, 28.8 mmol) in dioxane (32 mL) in a flask was heated to reflux (-100 C) overnight then cooled to room temperature, concentrated in vacuo on CELITE. This crude product was purified by flash chromatography using a 120g silica gel column (solid loading) eluting with 0-50% ethyl acetate/hexanes. Appropriate fractions (eluted near 25% EtOAc/hexanes) were collected and concentrated in vacuo to give 2-methoxy-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.47 g, 5.78 mmol, 60.2% yield) as a crystalline off-white solid. LCMS MH+ 250.1.

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-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)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 1462-37-9, Formula: C9H11BrO

Methyl 1-(2-(benzyloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate. Intermediate 4 (1.029 g, 4.0 mmol) was added to a suspension of NaH (192 mg of 60percent dispersion in mineral oil, 4.8 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 15 minutes, treated with benzyl 2-bromoethyl ether (0.7 mL, 4.4 mmol), stirred at room temperature for 2 hours, quenched with water, and extracted with ethyl acetate (2.x.50 mL). The organic layers were combined and washed (1N HCl), dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 3:1 hexanes/ethyl acetate) to provide the desired product as a colorless thick oil (1.19 g, 76percent yield). MS m/z 392(MH+); 1H NMR (500 MHz, CDCl3) delta 1.31 (m, 1H), 1.45 (m, 4H), 1.80 (d, J=13.12 Hz, 1H), 1.87 (m, 2H), 2.10 (m, 2H), 2.84 (m, 1H), 3.79 (t, J=5.34 Hz, 2H), 3.94 (s, 3H), 4.33 (t, J=5.49 Hz, 2H), 4.45 (s, 2H), 7.12 (s, 1H), 7.20 (m, 2H), 7.27 (m, 3H), 7.66 (d, J=8.55 Hz, 1H), 7.78 (d, J=8.55 Hz, 1H), 8.08 (s, 1H).

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

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150¡ã C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

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; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Wang, Yihan; Bohacek, Regine; US2003/114486; (2003); A1;,
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7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 7252-83-7

To a solution of o-thiocresol (16. 89g, 136mmo1) in acetone (130ml) is added potassium carbonate (20. 5g, 148mmol) and a solution of bromoacetaldehyde dimethylacetal (19.93g, 123mmol) in acetone (20ml) and the reaction mixture is stirred at ambient temperature overnight. The solids are filtered and washed with diethyl ether. The filtrate is concentrated and dissolved into ethyl acetate, washed successively with water, 0.5 N NaOH, and 2N NaOH. The combined aqueous fractions are extracted with dichloromethane. The combined organic fractions are dried over anhydrous MgS04, filtered and concentrated to afford 1- [ (2, 2-dimethoxyethyl) thio] -2-methyl-benzene as a brown oil (23.4g, 90%) that is used without further purification.’H NMR (CDC13) : 8= 7.33 (1H, brd), 7.19-7. 08 (3H, m), 4.56 (1H, t), 3.38 (6H, s), 3.10 (2H, d), 2.42 (3H, s).

The synthetic route of 7252-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
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Electric Literature of 134364-69-5,Some common heterocyclic compound, 134364-69-5, name is 2,3-Difluoroanisole, molecular formula is C7H6F2O, 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.

In a 1 L four-necked flask purged with nitrogen, 102 gOf 1, 2-difluoro-3-methoxybenzene was dissolved in 300 ml of THF and cooled to -78 C. To this was added 326 ml of a 2.4 M solution of butyllithium in hexane over 1 hour. After 1 hour, a solution of 133 g of trimethyl borate dissolved in 130 ml of THF was added dropwise over 1 hour. After 1 hour, the temperature of the system was brought to -30 C., 160 ml of 36% hydrochloric acid was added and the mixture was stirred for 2 hours. To the system, 500 ml of ethyl acetate and 200 ml of water were added and stirred, and the organic layer was separated. The mixture was further extracted with 200 ml of ethyl acetate and combined with the above organic layer, which was washed with 100 ml of saturated brine. After drying the solution with magnesium sulfate, the solvent was distilled off to obtain 133 g of the desired product as a white solid. Yield 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluoroanisole, its application will become more common.

Reference:
Patent; DIC CORPORATION; KUSUMOTO, TETSUO; AOKI, YOSHIO; (47 pag.)JP6136589; (2017); B2;,
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Related Products of 19500-02-8, 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 19500-02-8 as follows.

A solution of dimethyl acetylenedicarboxylate (17 g, 0.12 mol) in MeOH (20 mL) was added dropwise over 1 h to a solution of 3-methoxy-2-methylaniline (13.7 g, 0.1 mol) in MeOH (80 mL) stirred at r.t., and the mixture was stirred at r.t. for an additional 4 h. Evaporation of MeOH provided 7a (29.7 g; quantitative yield corresponds to 27.9 g) of yellowish oil (HPLC purity 93.5percent), which was used for the following step without further purification.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Radl, Stanislav; Rezkova, Hana; Obadalova, Iva; Srbek, Jan; B?icha?, Ji?i; Pekarek, Toma?; Synthesis; vol. 46; 7; (2014); p. 899 – 908;,
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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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2-ethoxyethane

1-Boc-piperazine (1.86 g, 10.0 mmol), 2-bromoethyl ethyl ether (1.92 g, 12.5 mmol) and K2CO3 (2.07 g, 15.0 mmol) in CH3CN (25 mL) were stirred at 70 C for 19 h. The mixture was allowed to cool to room temperature. The solids were filtered off and the filtrate was diluted with EtOAc (60 mL). The organic phase was washed with water (6 mL) and brine (6 mL), dried over Na2SO4, and evaporated to yield 2.45 g (95%) of tert-butyl 4-(2- ethoxyethyl)piperazine-1-carboxylate.1H NMR (600 MHz, DMSO-d6) delta ppm 3.46 (t, J=6.0 Hz, 2 H) 3.40 (q, J=7.0 Hz, 2 H) 3.28 (br. s., 4 H) 2.46 (t, J=6.0 Hz, 2 H) 2.34 (t, J=5.2 Hz, 4 H) 1.39 (s, 9 H) 1.09 (t, J=7.0 Hz, 3 H). MS (ESI+) m/z 259 [M+H]+ .

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 592-55-2.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (302 pag.)WO2018/11138; (2018); A1;,
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