Tag: M.W=200-300

874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, belongs to nitriles-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. Safety of 3-Bromo-2-fluorophenylacetonitrile

1.17 g of (3-bromo-2-fluorophenyl)acetonitrile and 15 mLof anhydrous DMSO were placed under nitrogen in an oven-dried flask. 459 mg of sodium hydride (60% dispersion in oil) were added, and the mixture was stirred at room temperature for 1 hour. 0.86 g of 2-chloroethyl ether dissolved with 2 ml anhydrous DMSO was added, and the mixture was stirred at room temperature overnight. 0.65 ml_ of glacial acetic acid was added, and the reaction was diluted into ethyl acetate, extracted with water and 5% sodium chloride, dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography on silica. The product fractions were concentrated and vacuum dried to give 730 mg of product. GCMS (M) 283; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 2.04 – 2.15 (m, 2 H) 2.17 – 2.25 (m, 2 H) 3.69 (td, J=12.08, 1.88 Hz, 2 H) 4.01 (dd, J=11.95, 2.82 Hz, 2 H) 7.27 (td, J=7.92, 1.07 Hz, 1 H) 7.47 – 7.55 (m, 1 H) 7.80 (ddd, J=8.12, 6.65, 1.61 Hz, 1 H).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
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Electric Literature of 79603-02-4,Some common heterocyclic compound, 79603-02-4, name is 2-Bromo-6-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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.

Intermediate 22: 2-Amino-6-bromobenzonitrile; [0189] 2-Bromo-6-nitrobenzonitrile (5g) was dissolved in a solution of methanol(lOOmL) and dioxane (65mL) and heated to reflux. Iron powder (4.6g) was added portion wise over 20 minutes and the mixture was heated at reflux for 4 hours. The mixture was allowed to cool to room temperature, filtered and the filtrate was evaporated under vacuum. The residue was triturated with water and the solid was collected by filtration to give the title compound as a light brown solid (3.8g).LCMS (Method E) r/t 3.01min (M+H) 197, 199

The synthetic route of 79603-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAFGEN CORPORATION; DYKE, Hazel, Joan; PALLIN, Thomas, David; CRAMP, Susan, Mary; WO2012/103333; (2012); A1;,
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Reference of 170230-29-2, 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 170230-29-2 as follows.

Description 26; 2-ethyl-4-biphenylcarboxylic acid (D26); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (270 mg, 1.30 mmol), phenylboronic acid (302 mg, 2.48 mmol), palladiumtetrakistriphenylphosphine (144 mg, 0.12 mmol) and potassium carbonate (514 mg, 3.72 mmol) in dimethylformamide (4 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature overnight before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-8 % EtOAc in hexane to give a colourless oil (272 mg). This material was added to ethanol (12 ml.) and water (3 ml.) followed by potassium hydroxide (730 mg, 13.0) mmol and the mixture heated to 90 0C overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (40 ml.) and 2M HCI (15 ml_). The organic layer was washed with further HCI (15 ml.) before it was dried (phase separator) and concentrated in vacuo. The resulting solid was purified by MDAP and the product containing fractions concentrated in vacuo. The residue was partitioned between ethyl acetate and 2M HCI. The organic phase was washed with further 2M HCI, dried (phase separator) and evaporated to give the title compound as a white solid (166 mg, 0.73 mmol). MS (ES”): C15H14O2 requires 226; found 225 (M- H+).

According to the analysis of related databases, 170230-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); 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 66389-80-8 as follows. SDS of cas: 66389-80-8

To a round-bottom flask equipped with a stir bar was added 18a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10mL/mmol). The reaction was refluxed and stirred in a pre-heated 75C oil-bath for 6h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. 4.2.4.5 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl)carbamate (19a) Yield: 65%. MP: 142-145C. 1H NMR (400MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1Hz, 2H, -ArH), 7.40 (t, J=6.1Hz, 1H, -NHCO-), 7.22 (d, J=8.1Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3)

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Zonghua; Rosenberg, Adam J.; Liu, Hui; Han, Junbin; Tu, Zhude; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 796 – 808;,
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Related Products of 17354-04-0, 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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

The chemical industry reduces the impact on the environment during synthesis 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Electric Literature of 79603-02-4, A common heterocyclic compound, 79603-02-4, name is 2-Bromo-6-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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.

Intermediate 11: 2-Nitro-6-cyclopropylbenzonitrile; [0176] 2-Bromo-6-nitrobenzonitrile (0.56g), cyclopropyl boronic acid (0.63g), palladium (II) acetate (0.055g), tricyclohexylphosphine (0.135g) and potassium phosphate tribasic (2.36g) were dissolved in a mixture of toluene (15mL) and water (3mL). The mixture was heated at 100C under nitrogen for 18 hours. The mixture was cooled and then partitioned between water and DCM. The organic solution was separated, dried with magnesium sulfate, filtered and the solvent was removed under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a light yellow solid (0.5 lg).NMR (CDCI3) delta 8.05 (d, IH), 7.64 (t, IH), 7.27 (d, IH), 2.52-2.45 (m, IH), 1.33-1.26 (m, 2H), 0.91-0.85 (m, 2H)

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; ZAFGEN CORPORATION; DYKE, Hazel, Joan; PALLIN, Thomas, David; CRAMP, Susan, Mary; WO2012/103333; (2012); A1;,
Nitrile – Wikipedia,
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Electric Literature of 17354-04-0, 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. 17354-04-0 name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, 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.

Example 6 5,6-dimethoxy-3H-indol-2-amine A solution of 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (0.22 g, 1 mmol) in ethanol (15 ml) was treated with tin chloride (0.50 g, 2.2 mmol) and heated to 70 C. for 72 hours. The reaction mixture was allowed to cool to room temperature, extracted with EtOAc and washed with 1N NaOH and water. The combined organic extracts were dried over MgSO4, filtered and concentrated. HPLC purification provided 5,6-dimethoxy-3H-indol-2-amine (12 mg, 6.2%). 1H NMR (400 MHz, DMSO) delta 11.82 (s, 1H), 9.80 (s, 1H), 9.54 (s, 1H), 7.11 (s, 1H), 6.82 (s, 1H), 4.10 (s, 2H), 3.77 (s, 3H), 3.73 (s, 3H). MS (APCI) m/z 193 (M+H)+.

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

Reference:
Patent; AbbVie Inc.; Pliushchev, Marina A.; Chiang, Gary G.; Pappano, William N.; Michaelides, Michael R.; Sweis, Ramzi F.; US2015/274660; (2015); 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. 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methoxybenzonitrile

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8- methoxyphenanthridin-6-amine (0.95g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

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; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
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Synthetic Route of 38791-62-7, The chemical industry reduces the impact on the environment during synthesis 38791-62-7, name is 4-Phenoxyphthalonitrile, I believe this compound will play a more active role in future production and life.

11.3 g of compound 1 was dissolved in 30 ml of methanol, added to 25 ml of 50% sodium hydroxide solution, heated to reflux for 48 h. After completion of the reaction, the pH was adjusted to about 3 with concentrated hydrochloric acid, precipitated by precipitation, filtered and dried to give 10.5 g of compound 2.

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

Reference:
Patent; BEIJING BETA PHARMA, INC.; (43 pag.)TWI582078; (2017); B;,
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Reference of 874285-03-7,Some common heterocyclic compound, 874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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-(3-bromo-2-fluorophenyl)acetonitrile (800 mg, 3.7 mmol,1 eq.) and (S)-1- iodo-2-(2-iodoethoxy)propane (1.27 g, 3.74 mmol, 1 eq.) were dissolved in dimethyl sulfoxide (10 ml_). Sodium hydride (331 mg, 8.3 mmol, 2.2 eq.) was added to the reaction mixture and stirred for 1 h at room temperature. The reaction mixture was diluted with water (10 ml_) and ethyl acetate (10 ml_), and the layers were separated. The organic phase was washed with 1 M HCI (1×10 ml_), water (1×10 ml_) and brine (1×10 ml_). The organic phase was concentrated under vacuum to afford a diastereomehc mixture of (2S,4R)-4- (3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2H-pyran-4-carbonitrile and (2S,4S)-4-(3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2/-/-pyran-4- carbonitrile (1 :1 ). The diastereomehc mixture was separated by reverse phase chromatography (40 – 90% acetonithle-water) to obtain the title compound (252 mg, 23%) as a single isomer. Stereochemistry confirmed by NMR. [2SAR)- 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.26 (d, J=6.2 Hz, 3 H) 1.81 (dd, J=13.2, 11.0 Hz, 1 H) 2.08 – 2.26 (m, 3 H) 3.89 – 4.02 (m, 2H) 4.04 – 4.16 (m, 1 H) 6.99 – 7.13 (m, 1 H) 7.32-7.44 (m, 1 H) (s, 1 H) 7.51 – 7.63 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%). (2S,4S): 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.22 (d, J=6.2 Hz, 3 H) 2.05 (dd, J=14.5, 10.7 Hz, 1 H) 2.25-2.44 (m, 1 H) 2.49 – 2.63 (m, 2 H) 3.44 – 3.59 (m, 2H) 3.86 – 3.99 (m, 1 H) 7.02 – 7.13 (m, 1 H) 7.19-7.31 (m, 1 H) (s, 1 H) 7.53-7.64 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts