Author: Jessica.F

Application of 327056-73-5, 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 327056-73-5 as follows.

Preparation 23: 3-Chloro-5-[2-methoxy-5-(trifluoromethoxy)phenoxylbenzonitrile To a solution of the compound of preparation 22 (270mg, 1.30mmol) in DMF (5mL) was added cesium carbonate (551 mg, 1.69mmol) at rt. The reaction mixture was stirred for 5 min and the compound from preparation 37 (1.69mmol, 263mg) was added. The mixture was then heated at 85 0C for 3h and cooled to rt. Brine was added followed by water and the aqueous phase was extracted with EtOAc. The organic extract was dried over magnesium sulfate and the solvent was concentrated in vacuo to afford the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate (88:12) as eluent afforded the desired product, 360mg (81%). LRMS (APCI) 343 [MH”]; Preparations 2-7 To a solution of the appropriate phenol (1 eq.) in DMF (0.8 to 1.85mLmmor1) was added cesium carbonate (1-2 eq.) at rt and the solution was stirred for 10 min. The compound from preparation 37 (1.3 eq.) was then added and the reaction mixture was heated at 85 C for up to 48h (reactions monitored by tic). The solvent was removed in vacuo and the residue was partitioned between EtOAc (5OmL) and brine (5OmL). The phases were separated and the aqueous layer extracted with EtOAc (1 OmL). The organic extracts were combined, dried over magnesium sulfate and the solvent was removed in vacuo to give the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate as eluent afforded the desired product. EPO A = 4-hydroxy-3-methoxybenzonitrile prepared as described in Synthesis 1989(6); 451-2. The product was isolated after trituration with methanol.B = potassium carbonate was used in place of cesium carbonate.

According to the analysis of related databases, 327056-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2006/67587; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, Formula: C4H7ClN2

General procedure: Thecarboxylic acid intermediate (1 eq) was dissolved into DCM (1-3 mL/1 mmol) andcooled to 0C. HATU (2 eq) and DIPEA (4 eq) were then added and reaction wasstirred at 0C for 5-10 min. 2-aminoacetonitrile bisulfate (2-5 eq) was thenadded and reaction was allowed to warm and stir at room temperature overnight.Upon completion, the reaction was poured into a 1N HCl(aq) solutionand extracted with DCM. The combined organic layers were washed with 1N HCl(aq)solution, NaHCO3(aq) solution, and brine then dried over MgSO4,and concentrated. The crude material was purified by flash chromatography(0-100% EtOAc:Hexane gradient). 15-89%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Zwicker, Jeffery D.; Diaz, Nicolas A.; Guerra, Alfredo J.; Kirchhoff, Paul D.; Wen, Bo; Sun, Duxin; Carruthers, Vern B.; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1972 – 1980;,
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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. 57418-97-0, name is 4-Bromo-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromo-3-chlorobenzonitrile

Step a. A mixture of 4-bromo-3-chlorobenzonitrile (150 mg, 0.69 mmol), tert-butyl 4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate (Intermediate 2, 287 mg, 0.83 mmol) and K2C03 (238 mg, 1.73 mmol) in 1,4-dioxane (5.4 ml) and water (0.6 ml) was degassed by nitrogen bubbling for 5 min. Pd(PPh3)4 (79 mg, 0.069 mmol) was then added. The mixture was heated at reflux for 18 h and then cooled to rt. The mixture was filtered on a silica pad and washed with EtOAc (200 ml). The filtrate was evaporated under reduced pressure. The residue (500 mg) was dissolved in DCM and purified by flash chromatography on silica gel using hexane/EtOAc (90: 10) to give tert-butyl 4- (2-chloro-4-cyanophenyl)isoindoline-2-carboxylate (242 mg, 99%) as a bright yellow solid. LCMS: Method I, 3.66 min, MS: ES+ 355, 357; NMR (400 MHz, CDC13) delta ppm 7.80 (m, 1H), 7.63 (m, 1H), 7.33-7.41 (m, 3 H), 7.14 (m, 1H), 4.77 (m, 2 H), 4.56 (m, 2 H), 1.49 (m, 9 H).

The synthetic route of 57418-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); 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 179897-89-3 as follows. Formula: C7H3BrFN

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2CO3 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110 C. for 16 hrs. Cool to room temperature, filter the solid, and concentrate the filtrate to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=1:3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

According to the analysis of related databases, 179897-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35704-19-9, name is N-(4-Cyanophenyl)acetamide, 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 35704-19-9, name: N-(4-Cyanophenyl)acetamide

STR105 To a solution of 4-acetamidobenzonitrile (9.40 g) in concentrated sulfuric acid (80 ml) was added potassium nitrate in small portions at a temperature not exceeding 10 C. The reaction mixture was stirred at 5-10 C. for 2 hours and poured into ice-water and the separated crystals were collected by suction. To the crystals was added 4N hydrochloric acid (100 ml) and the mixture was refluxed for 2 hours. After cooling to room temperature, the crystals were recovered by filtration, washed with water and dried under reduced pressure to give 7.22 g of 4-amino-3-nitrobenzonitrile. Mass spectrum (m/z): 163 (M+). NMR (DMSO-d6) delta: 7.00-7.14 (1H, m), 7.60-8.10 (3H, m), 8.40-8.60 (1H, m).

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, N-(4-Cyanophenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5162318; (1992); A;,
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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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

According to the method described in Embodiment 1,Add 1d (0.5mmol, 88mg) and 2f (1.25mmol) to a 15mL pressure tube.190mg),Dichloro (pentamethylcyclopentadienyl yl)rhodium (III) dimer (0.025mmol, 15mg), copper acetate monohydrate (1mmol, 200mg),Cesium acetate (0.25mmol, 48mg) and 1,2-dichloroethane (2 mL), under an air atmosphere and the reaction tube was sealed, and then placed in an oil bath at 80 reaction was stirred 14h. The reaction was quenched with 10mL of water was added, extracted with ethyl acetate (10mL ¡Á 3), then the organic phase was washed with water and saturated brine successively, dried over anhydrous sodium sulfate. Filtration, rotary evaporation, separating silica gel column (petroleum ether / ethyl acetate = 5/1) to give a yellow solid 3df (136mg, 70%).

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Fan Xuesen; Guo Chenhao; Zhang Beibei; Zhang Xinying; Li Bin; (17 pag.)CN108997298; (2018); A;,
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Reference of 874-97-5, 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. 874-97-5, name is 3-Cyanobenzyl alcohol belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure 2: In a vial the acid (1.32 mmol), dicyclohexylcarbodiimide (DCC; 1.45 mmol) and the alcohol (1.32 mmol) were dissolved in dry THF (5mL). The reaction mixture was stirred at room temperature overnight, and then filtered. The filtrate was diluted with dichloromethane and washed with water (2x) followed by brine, dried over sodium sulfate and concentrated to a crude residue, which was purified by flash chromatography.

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-Cyanobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Titchenell, Paul M.; Hollis Showalter; Pons, Jean-Francois; Barber, Alistair J.; Jin, Yafei; Antonetti, David A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 3034 – 3038;,
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17983-30-1, name is 3-Oxocyclohexanecarbonitrile, 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-Oxocyclohexanecarbonitrile

Example 2Conversion of 3-cyanocyclohexanone to 3-aminomethyl-1-cyclohexylamineThe apparatus used consisted of 8 tubular reactors connected in series. The dimensions of the first two tubes (C1-C2) were 1500¡Á6¡Á1 mm. The dimensions of the 6 further tubes (C3-C8) were 2000¡Á8¡Á1.5 mm. The first two reactors (C1-C2) were charged with 15.7 g of TiO2 extrudates with a diameter of 1.5 mm, the remaining 6 reactors each with approx. 85 g of a hydrogenation catalyst (Mn3O4 5-6.2%, Na2O 0-0.5%, H3PO4 2.8-3.8%, remainder Co+CoO) which had been reduced with hydrogen at 280 C. at a pressure of 1 bar for 24 hours.The temperature of the first two reactors C1-C2 was adjusted to 60 C. The temperature of reactors C3-C4 was 90 C., the temperature of reactors C5-C6 was 115 C. and the temperature of reactors C7-C8 was set to 130 C. Between reactors C2 and C3, hydrogen was fed into the reaction mixture under pressure. The operating pressure was 230 bar.23 g/h of a mixture of THF and 3-cyanocyclohexanone in a ratio of 1:1 together with 73 g/h of NH3 were pumped into the first reactor (C1), and 17 standard liters/h of hydrogen were also fed in upstream of reactor C3. The reaction output was decompressed through a regulating valve. In a downstream phase separator, hydrogen was then removed and ammonia was evaporated off.A total of 592 g of 3-cyanocyclohexanone were used. The crude output was distilled through a 60 cm column with random packing at <1 mbar. The product distilled over at 54 C. 433.7 g of 3-aminomethyl-1-cyclohexylamine were obtained as a mixture of cis/trans isomers with a purity of 99.5% (cis: 85.6, trans: 14.1; CT ratio: 86:14). The yield in the hydrogenation stage was 84% including the product content in the different fractions and 70.4% of pure product after the distillation.The mixture of the isomeric diamines was characterized by GC-MS, NMR and elemental analysis.13C-NMR (125 MHz, DMSO): 50.33 (cis-AMCHA), 48.57 (cis-AMCHA), 47.22 (trans-AMCHA), 45.35 (trans-AMCHA) 41.26 (cis-AMCHA), 40.43 (cis-AMCHA), 38.02 (trans-AMCHA), 36.88 (cis-AMCHA), 35.03 (trans-AMCHA), 34.53 (trans-AMCHA), 29.87 (cis-AMCHA), 29.44 (trans-AMCHA), 24.61 (cis-AMCHA), 19.66 (trans-AMCHA).In the GC-MS, by the method of 30m db35 MS 0.25 micrometer, start temperature 60 C., temperature ramp 5 C./min to 280 C. and bakeout at this temperature for 30 min, two main peaks were detected, retention times 19.07 min (85.6 area %) and 19.2 min (14.1 area %).The following fragment distributions were obtained (M+=128 corresponds to the particular molecular peak):Peak 1:m/z (%)=18(5), 27(5), 28(14), 29(7), 30(59), 39(9), 41(15), 42(13), 43(48), 44(17), 53(5), 54(12), 55(11), 56(100), 57(15), 58(9), 67(23), 68(11), 69(17), 70(18), 71(3), 77(4), 79(6), 80(3), 81(9), 82(28), 83(9), 85(4), 94(3), 96(8), 98(79), 99(36), 110(6), 111(19), 112(3)Peak 2:m/z (%)=18(4), 27(6), 28(14), 29(7), 30(61), 39(10), 41(16), 42(15), 43(45), 44(12), 53(6), 54(11), 55(11), 56(100), 57(32), 58(9), 67(20), 68(11), 69(20), 70(18), 71(3), 77(4), 79(7), 80(3), 81(9), 82(25), 83(14), 84(3), 85(3), 94(3), 96(10), 98(68), 99(22), 110(7), 111(41), 112(5)To determine the elemental analyses, an Elementar Vario EI III automatic analyzer was used.The elemental analysis gave_C=64.8 (expected: 65.6); N=22.1 (expected: 21.9); H=12.8 (expected: 12.6) g/100 g The synthetic route of 17983-30-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASF SE; US2011/124919; (2011); 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. 115661-37-5, name is 2-Amino-3-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 115661-37-5

To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) over 10 min at 0C. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
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Reference of 501420-63-9,Some common heterocyclic compound, 501420-63-9, name is 2-(3-Bromo-4-fluorophenyl)acetonitrile, 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.

(3-Bromo-4-fluorophenyl)acetonitrile (4.00 g, 18.32 mmol), bis(pinacolato)diboron (5.22 g, 20.15 mmol), potassium acetate (55.86 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.2% of Pd) (393.53 mg, 0.55 mmol) were dissolved in oxygen-free 1,4-dioxane (40 ml, max. 0.005% of water) under argon. The reaction mixture was subsequently heated at a temperature of 130 C. for 90 min. When the reaction conversion was complete, the mixture was filtered through kieselguhr. The filtrate was diluted with dichloromethane (200 ml) and water (50 ml) and extracted. The organic phase was dried over sodium sulfate, subsequently filtered and evaporated to dryness in vacuo, giving [4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile as oil (7.59 g, purity 81%, MS: 262.2 [M+H+]), which was reacted further without further work-up.

The synthetic route of 501420-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; FUCHSS, Thomas; EMDE, Ulrich; BUCHSTALLER, Hans-Peter; MEDERSKI, Werner; (224 pag.)US2016/83401; (2016); A1;,
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