Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 590-17-0, name is 2-Bromoacetonitrile, belongs to nitriles-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 590-17-0, category: nitriles-buliding-blocks

Screening of A3a in existing CWR protocols – standard room temperature conditions: Scheme A52. Screening of A3a in RT-CWR conditions.Benzaldehyde (100 iL, 1.0 mmol, 1.0 equiv.), bromoacetonitrile (86 iL, 1.3 mmol, 1.3 equiv.), phenylsilane (172 iL, 1.3 mmol, 1.3 equiv.) and DIPEA (244 pL, 1.4 mmol, 1.4 equiv.) were reacted using A3a (23 mg, 0.1 mmol, 10 mol %) and 4-nitrobenzoic acid (17 mg, 0.1 mmol, 10 mol %) in ethyl acetate (0.33 mL) at RTfor24 h (Scheme S2). The crude product was analyzed by 1H NMR spectroscopy, which showed 100%conversion to product and an E/Z ratio of 93:7.The crude product was purified via flash column chromatography to afford pure product as a colorless oil (126 mg, 98%, E/Z93:7).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DUBLIN CITY UNIVERSITY; O’BRIEN, Christopher; WO2014/140353; (2014); A1;,
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Reference of 72635-78-0,Some common heterocyclic compound, 72635-78-0, name is 3-Amino-4-bromobenzonitrile, molecular formula is C7H5BrN2, 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.

The following intermediates as shown in Table 48 are synthesized in a similar fashion from the appropriate intermediatesStep 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-bromobenzonitrile, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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Related Products of 331-62-4, 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 331-62-4 as follows.

BBr3 (20 mL, 0.211 mol) was added to 3-fluoro-4-methoxybenzonitrile (15.6 g, 0.103 mol) in dichloromethane (100 mL) at 0 ¡ãC. The mixture was refluxed for 3 days under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure gave 13.3 g (94percent) of the product as a gray solid. :H NMR (400 MHz, CDC13) delta 7.38-7.42 (m, 2H), 7.09 (dd, J= 8.8 Hz, 8.4 Hz, 1H), 5.68 (s, 1H).

According to the analysis of related databases, 331-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Li; HU, Yuandong; YU, Rong; HU, Wei; ZHAO, Na; PENG, Yong; LUO, Hong; HAN, Yongxin; WO2013/97773; (2013); A1;,
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These common heterocyclic compound, 13989-82-7, name is 4-(Dimethylamino)butanenitrile, 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. SDS of cas: 13989-82-7

4-(Dimethylamino)butyronitrile (4.4 g) was dissolved in tetrahydrofuran (40 mL), and a 1 mol/L borane/tetrahydrofuran solution (40 mL) was added dropwise under ice-cooling. After the completion of the reaction, water was added to the reaction solution. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography. A hexane:ethyl acetate=1:1 effluent fraction was concentrated to give (4-(dimethylamino)butyronitrile-N1)trihydroboron (2.8 g). The reaction was carried out in the same manner as in Example 82 using N,N-dimethyl-2,3-dimethylbenzamide (3.9 g) and (4-(dimethylamino)butyronitrile-N1)trihydroboron to give (3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g). (3-(3-(Dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g) was dissolved in acetone (20 mL), and conc. hydrochloric acid (1 mL) was added at room temperature. After the completion of the reaction, the solvent was concentrated. Toluene was added to the obtained residue, and the mixture was extracted with water. Potassium carbonate was added to basify the aqueous layer, and the mixture was extracted with chloroform and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography (NH silica gel, Fuji Silysia Chemical Ltd.). A chloroform effluent fraction was concentrated, and diisopropyl ether was added to the obtained residue. The precipitated crystals were collected by filtration to give 3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one (1.5 g). melting point: 105-106C.1H-NMR(CDCl3) delta: 1.79-1.89(2H,m), 2.34(6H,s), 2.39(2H,t,J=6Hz), 2.49(3H,s), 2.69(2H,t,J=6Hz), 6.34(1H,s), 7.31(1H,t,J=8Hz), 7.42(1H,dd,J=1Hz,7Hz), 8.23(1H,d,J=8Hz), 11.37(1H,brs).

The synthetic route of 4-(Dimethylamino)butanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1396488; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 76574-39-5, 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. 76574-39-5, name is 2-(2-Bromo-6-chlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(2-Bromo-.6-chlorophenyl)acetonitrile (450 mg, 2.0 mmol) (43-1), 3- pyridylboronic acid (251 mg, 2.1 mmol) (43-2), potassium fluoride (230 mg, 3.9 inmol), 1,4- dioxane (12 mL), methanol (3.6 rnL), Pd2(dba)3 (71 rng, 0.080 mrnol) and dicyciohexyl-12-(2,6- dimethoxyphenyl)phenyi]phosphane (32 Ing, 0.080 mmol) were combined under an atmosphere of nitrogen and the resulting mixture was heated at 80 C After 16 h, the reaction was filtered and concentrated under reduced pressure. The resulting oil was dissolved in DCM and purified by silica gel chromatography eluting with methanol/dichloromethane to afford 317 mg (71%) 2- [2.-chloro-6-(-pyridyl)phenyllacetonitriie (43-3). LCMS (ESI): [M+Hf = 229.1

The synthetic route of 2-(2-Bromo-6-chlorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); A1;,
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Synthetic Route of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

A mixture of 100 mg (0.46 mmol) 4-bromo-2,5-difluoro-benzonitrile, 146 mg (0.78 mmol) intermediate 111.14, 0.2 ml (1 .42 mmol) DIPEA and DMSO is heated to 100C for 5.5 h. After cooling to RT the reaction mixture is diluted with ACN and water and purified by HPLC giving rise to 1 16 mg 4-bromo-2-[4-(4-cyanophenyl)piperazin-1 -yl]- 5-fluoro-benzonitrile

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; BLUM, Andreas; PETERS, Stefan; (80 pag.)WO2017/148518; (2017); A1;,
Nitrile – Wikipedia,
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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 4354-73-8 as follows. Recommanded Product: 4354-73-8

General procedure: Knoevenagel adduct 1 and 2 equivalents of a propargyl bromide derivative 2 were dissolved in anhydrous DMF (0.5 M with respect to the limiting reagent). Finely ground K2CO3 (3 equivalents) was then added to the solution and stirred at room temperature until the limiting reagent was consumed (monitored by TLC; 30 min-2 hrs.). The solution was then diluted with EtOAc and washed with H2O five times. The organic layer was then washed with brine and dried with Na2SO4. The solvent was removed under reduced pressure and the crude material purified via column chromatography (hexane-ethyl acetate) unless otherwise noted. Using the foregoing method, compounds 3a-3f and 3h-3m were prepared, and are described in further detail herein below Pale yellow oil, 93% yield, 2.34 g. Purified using 10% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) delta 6.30 (dq, J=3.8, 2.0 Hz, 1H), 2.97 (d, J=2.6 Hz, 2H), 2.35 (t, J=2.5 Hz, 1H), 2.23-2.11 (m, 5H), 1.79-1.72 (m, 2H), 1.63 (pd, J=6.9, 6.2, 4.1 Hz, 2H). 13C NMR (125 MHz, CDCl) delta 131.0, 127.0, 113.9, 75.2, 74.9, 43.4, 28.8, 25.4, 24.5, 22.3, 21.3. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C12H13N2 185.1073; Found 185.1080. [M+Na]+ Calcd for C12H12N2Na 207.0893; Found 207.0883. Rf=0.51 (20% EtOAc in hexane)

According to the analysis of related databases, 4354-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Florida Research Foundation, Inc.; Grenning, Alexander James; Scott, Sarah; (66 pag.)US10287239; (2019); B1;,
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Related Products of 39095-25-5,Some common heterocyclic compound, 39095-25-5, name is 2,5-Dimethylterephthalonitrile, molecular formula is C10H8N2, 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 100ml 4-neck reactor 2,5-dimethyl-terephthalonitrile 2.3g, Carbon tetrachloride 23ml, NBS 5.3g, AIBN 0.07g 1 hour reaction at charged 75C It was. After completion of the reaction, it was allowed to cool to room temperature. Wash the residue and the reaction solution was filtered with carbon tetrachloride It was. Crude product is obtained in the oil and the filtrate was concentrated. The addition of methanol and allowed to crystallize the crude product. Taken out crystals were filtered off, 1,4-dicyano-2,5-bis-bromo methyl benzene was obtained 0.57g. In 50ml 3-necked reactor 1,4-dicyano-2,5-bis bromomethylbenzene 0.55g, Triethyl phosphite 0.61g was stirred and heated to charged 100-110 . At this temperature the reaction was carried out for 2 hours. Was allowed to cool to room temperature, and purified on a silica gel column 2,5-dicyano-1,4-bis (diethyl phosphonyl methyl) benzene was obtained 0.45g. 50ml 3-necked reactor to 2,5-dicyano-1,4-bis (diethyl phosphonyl methyl) benzene 0.45g, DMF (dehydration) 15ml, 4 formylpyridine 0.28g They were charged. After nitrogen substitution, Potassium t- butoxide 0.35g It was changed to green-brown solution and dropping the 5mlDMF solution slowly. It was allowed to react for 3 hours at 60 . The reaction mixture was extracted with chloroform and released into the water. The reaction mixture was concentrated to give crude product. The crude product was purified on a silica gel column (toluene / acetone 1/1) and the resulting solid to yield 0.08g of intermediate 45 and purified construed methanol. A synthesis flow of this intermediate 45 below

The synthetic route of 39095-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICOH COMPANY LIMITED; YAMADA CHEMICAL COMPANY LIMITED; HIRANO, SHIGENOBU; YASHIRO, TOHRU; MANABE, YOUSUKE; HAYASHI, SATOSHI; (35 pag.)JP5900813; (2016); B2;,
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Electric Literature of 2286-54-6, A common heterocyclic compound, 2286-54-6, name is 3,3-Diphenylpropanenitrile, molecular formula is C15H13N, 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.

In the glove box, 0.01 mmol of nickel chloride was added, 0.52 mmol of diphenylphosphine oxide, 1.5 equivalents of t-BuOK (potassium tert-butoxide),Add to the Schlenk reaction tube in turn, then Add 0.4mmol 1, 1-diphenylpropionitrile compound, Vacuum and backfill nitrogen; under a nitrogen atmosphere, add 3 ml of 1,4-dioxane to the solvent. The reaction was continued at 120 C for 16 h. After the reaction is completed, it is cooled to room temperature and separated by column chromatography. That is the target product: 1,1-diphenylethyldiphenylphosphine oxide, yield 87%.

The synthetic route of 2286-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University; Zhang Jishu; Qi Tafamingrenqingqiubugongkaixingming; (13 pag.)CN109438512; (2019); A;,
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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. 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (compound B) (10.0 g, 32.9 mmol), potassium acetate (9.7 g, 99.0 mmol), XPhos (0.078 g, 0.16 mmol), XPhos-Pd-G2 (0.068 g, 0.082 mmol) and tetrahydroxydiboron (4.4 g, 49.3 mmol) were added to an oven dried glass reactor with a positive N2 pressure. The vessel was sealed and then evacuated and backfilled with N2 (four times). MeOH (100 mL, degassed) was added via syringe, followed by the addition of ethylene glycol (5.5 mL, 99.0 mmol). The reaction was then heated to 64-66 C until the starting material was consumed (as monitored by TLC). The solvent was concentrated in vacuo and the crude reaction product was dissolved in EtOAc (50 mL) and then transferred to a separatory funnel. H20 was added (50 mL), the layers were separated and the aqueous layer was further extracted with more EtOAc (30 mL). The combined organic layers were washed once with 1 M HCI (30 mL) and once with H20 (30 mL), then dried over Na2S04 and concentrated in vacuo. The solid residue was purified twice by recrystallization in hot methanol, thus affording pure 4-[(1-hydroxy-1 ,3-dihydro- 2,1-benzoxaborol-5-yl)oxy]benzonitrile (crisaborole) (6.6 g, 26.3 mmol) as a white solid. Yield: 80% (calculated from 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile) Purity by HPLC: > 99.9% 1H-NMR (200 MHz, DMSO-d6, delta ppm): 9.22 (1 H, s); 7.85-7.83 (2H, m, J= 8.9 Hz); 7.81 -7.79 (1 H, d, J= 8.1 Hz); 7.15-7.13 (3H, m); 7.10-7.08 (1 H, dd, J= 8.1 , 2.1 Hz); 4.97 (2H, s) 13C-NMR (50 MHz, DMSO-d6, ppm): 160.6; 157.1 ; 156.6; 134.7; 132.6; 1 18.9; 1 18.6; 1 12.7; 105.5; 69.7.] FT-IR: 2222.9, 1600.8, 1501.2, 1467.5, 1406.0, 1390.9, 1360.6, 1244.7, 1 167.3, 1 1 16.1 , 1010.7, 937.3, 892.5

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; LABORATORIOS LESVI, SL; HUGUET CLOTET, Juan; OZORES VITURRO, Lidia; RODRIGUEZ ROPERO, Sergio; DALMASES BARJOAN, Pere; (39 pag.)WO2018/115362; (2018); A1;,
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