Author: Jessica.F

These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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. Quality Control of 1-Bromo-4-(difluoromethoxy)benzene

Step 4) 1-difluoromethoxy-4-{3-[3-(2-methoxy-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (1.00 g, 2.70 mmol) was dissolved in THF (5 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (5 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (1.20 gm, 5.38 mmol), copper iodide (70 mg, 0.262 mmol), tetrakis(triphenylphosphine)palladium (140 mg, 0.120 mmol) and triethylamine (5.8 g, 98 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%-10% EtOAc in hexanes) afforded an oil 882 mg (46%). This material was used in next step without further characterization.

The synthetic route of 1-Bromo-4-(difluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
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Application of 261762-35-0, A common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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.

Step 1: Preparation of 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8- azaspiro[4.5]decane To a mixture of 5-bromo-1,2-difluoro-3-methoxy-benzene (1.1 g, 4.93 mmol), 1,4-dioxa-8- azaspiro[4.5]decane (0.85 g, 5.92 mmol) and t-BuONa (0.95 g, 9.86 mmol) in 1,4-dioxane (10 mL) was added Pd2(dba)3 (92 mg, 0.10 mmol) and Ru-Phos (92 mg, 0.20 mmol) successively under N2. After being heated at 100 oC with stirring overnight, the reaction mixture was cooled down to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.57 g) which was used in the next step directly without further purification.

The synthetic route of 261762-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 C9H13NO

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6851-80-5, its application will become more common.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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Related Products of 93919-56-3,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.

2-Amino-3,5-difluorobenzoic acid (500 mg; 2.89 mmol), 10 ml of dry DCM, and TEA (1.61 ml; 11.55 mmol) were placed in a reaction flask under nitrogen. 4- (Trifluoromethoxy)benzylamine (0.529 ml; 3.47 mmol) was added slowly and then T3P (3.4 ml; 5.78 mmol; 50 % in EtOAc) was added keeping the temperature at rt. The mixture was stirred at rt overnight. The reaction mixture was diluted with DCM and washed three times with water. The organic phase was dried with a phase separator and evaporated to dryness to yield 1.09 g of 2-amino-3)5-difluoro-N-(4-(trifluoromethoxy)benzyl)benzamide. 1H-NMR (400 MHz, -DMSO): delta 3.33 (s, 6H), 4.45 (d, 2H), 6.24 (s, 2H), 7.22-7.40 (m, 4H), 7.41-7.51 (m, 2H), 9.02 (t, 1H).

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

Reference:
Patent; ORION CORPORATION; PRUSIS, Peteris; HOeGLUND, Lisa; TOeRMAKANGAS, Olli; HIETANEN, Ari; ARVELA, Riina; VESALAINEN, Anniina; HEIKKINEN, Terhi; WO2015/169999; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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 17715-69-4, Computed Properties of C8H9BrO2

General procedure: A solution of 4-methoxybromobenzene (2.67 mmol)and cyclopent-2-en-1-one (3.2 mmol) in DMSO was stirred at ambient temperaturefor 10 min under nitrogen, and treated with Na2CO3 (8.01mmol) and tri-tert-butylphosphonium tetrafluoroborate (0.53 mmol).The reaction mixture was degassed with nitrogen for 10 min and treated withPd(PPh3)2Cl2 (0.13 mmol) and X-Phos (0.26mol), and stirred at 100 0C for 12 h. The reaction mixture was cooledto ambient temperature, diluted with water, and extracted with AcOEt (3 x 50ml). The combined organic layers were washed with brine, dried over anhydrousNa2SO4, and evaporated. Flash chromatograph on silica gel(AcOEt:cyclohexane 1:3) provided the Heck coupling product as brown solid (340mg, 68percent).

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, 1-Bromo-2,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gowala, Tarak Nath; Pabba, Jagadish; Tetrahedron Letters; vol. 56; 14; (2015); p. 1801 – 1804;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

41. Reaction of but-3-en-1-ol and (benzyloxy)acetaldehyde in the presence of sulfuric acid provided 2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-ol, which was oxidized with pyridinium chlorochromate to afford 2-[(benzyloxy)methyl]tetrahydro-4H-pyran-4-one. Subsequent reductive amination with 1-(2,4-dimethoxyphenyl)methanamine and lithium borohydride gave cis-2-[(benzyloxy)methyl]-N-(2,4-dimethoxybenzyl)tetrahydro-2H-pyran-4-amine. This was reacted with C13 and triethylamine, and the product was deprotected using trifluoroacetic acid to yield N-{cis-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-yl}-6-chloro-3-nitroquinolin-4-am ine; hydrogenation of the nitro group over platinum(IV) oxide afforded N4-{cis-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-yl}-6-chloroquinoline-3,4-diamine.

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 20781-20-8.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6F3NO

Stepl : 1-azido-2-(trifluoromethoxy)benzene (27a) Concentrated HCl (7.9 mL) was added to a solution of 2-(trifluoromethoxy)aniline (1.1 mL, 7.9 mmol) in EtOAc (26 mL) at 0 C. After 10min, a solution of sodium nitrite (1.6 g, 23.7 mmol) dissolved in water (4.6 mL) was added slowly over 5 min. The mixture was stirred for 30min, and then treated with a solution of sodium azide (1.5 g, 23.7 mmol) in water (5.3 mL) slowly over 5min. The reaction was stirred for 1 h then treated with phosphate buffer saline (pH 7.4, 50 mL). The mixture was extracted with EtOAc, the organics were washed with brine, dried over Na2S04 and concentrated to give compound 27a.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KROPF, Jeffrey, E.; SCHMITT, Aaron; WATKINS, William, J.; XU, Jianjun; GEGE, Christian; (92 pag.)WO2016/96116; (2016); 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 768-70-7 as follows. category: ethers-buliding-blocks

Weigh 10 mg of the above catalyst, 0.5 mmol of compound 1, and 1 mmol of K3PO4 solids into a 10 ml Shrek tube.Seal the nozzle with a rubber stopper and protect it with vacuum argon.Using a microsampler, 1 mmol of Compound 2 and 5 ml of DMF solvent were injected into the reaction system through a rubber stopper.Place the reaction tube in an oil bath at 160 C.After 5h of reaction, the catalyst was filtered off,Obtain a uniform reaction solution, wash with water to remove DMF,Then, it is dried and separated by column chromatography to obtain 2- (3-methoxyphenyl) benzofuran of the following structural formula 5,NMR yield was 91%.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Tsingtao Biological Energies And Process Institute; Yang Yong; Ji Guijie; Duan Yanan; Zhang Shaochun; (10 pag.)CN110386909; (2019); A;,
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Related Products of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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 11 (Z)-3-((2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)-1-(3,4,5-trimethoxyphenyl) prop-2-en-1-one (10x) To a stirred solution of (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)aniline (5d) (100 mg, 0.317 mmol) in ethanol (5 ml) 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one (6x) (69.7 mg, 0.317 mmol) was added. The reaction mixture was stirred at a temperature of 30 C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (1:1) as a solvent system. Then water (10 ml) was added to reaction mixture. A yellow colour solid appears which was filtered and washed with ethanol. (yield: 120 mg, 70%); mp: 120-122 C.; 1H NMR (CDCl3, 500 MHz) delta (ppm): 12.09 (d, J=12.5 Hz, NH), 7.23-7.21 (m, 1H), 7.2 (s, 2H), 7.15 (d, J=1.8 Hz, 1H), 6.96 (dd, J=6.56 Hz, 1.8 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.54 (s, 2H), 6.49 (q, J=12.2 Hz, 2.44 Hz, 2H), 5.92 (d, J=7.9 Hz, 1H), 3.96 (s, 3H), 3.93 (s, 6H), 3.9 (s, 3H), 3.85 (s, 3H), 3.71 (s, 3H); FABMAS:(M+H)=536.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, its application will become more common.

Reference:
Patent; Council of Scientific and Industrial Research; Ahmed, Kamal; Gajjela, Bharath Kumar; Anver, Basha Shaik; Vangala, Santhosh Reddy; Mahesh, Rasala; US2015/322009; (2015); A1;,
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Electric Literature of 79128-08-8,Some common heterocyclic compound, 79128-08-8, name is 1,3-Diisopropoxybenzene, molecular formula is C12H18O2, 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.

at 0 adding n-butyllithium (2.5M, 40mL, 100mmol) in hexane solution was added to the compoundIt was 2 (19.4g, 100mmol) in THF (10 mL), and the mixture was stirred at 15 2 hours.After the mixture was cooled to 0 again, iodine (25.4g, 100mmol) were added thereto, and 10 The mixture was stirred for 16 hours. Saturated aqueous solution of sodium sulfite (50 mL) was added to the reaction solution toThe reaction was quenched, and the organic solvent was removed under reduced pressure. Thereafter, ethyl acetate (50mL × 3) extraction residue.The organic layer was dehydrated over sodium sulfate and concentrated. By using petroleum ether as eluent, concentrate purified by silica gel columnThereof, whereby the compound 3.

The synthetic route of 79128-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Polypropylene Corporation; Tanna, Akirahisashi; Sato, Naomasa; Konishi, Yohei; Oishi, Yasuo; (27 pag.)CN105593235; (2016); A;,
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