Nitriles-buliding-blocks

These common heterocyclic compound, 1250444-23-5, name is 3-Bromo-2,6-difluorobenzonitrile, 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. 1250444-23-5

3-bromo-2,6-difluorobenzonitrile and triethyl phosphite in a 1: 8.0 proportion feeding, N2 Protection, reaction temperature 100 , reaction was carried out under the lighting conditions. TLC monitored the reaction to the raw material 30h point disappears. The product was distilled under reduced pressure, the oil bath temperature to 100 deg.] C, the low boiling fraction was distilled off. Again the product distilled under reduced pressure, the oil bath temperature to 190C, distilled high boiling fraction, taken when the steam temperature 135-145C fraction, the evaporated fraction dissolved in ethyl acetate, respectively, with 10% Na2CO3, Washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered and rotary evaporated to give a yellow oily liquid product, in 83% yield.

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 1250444-23-5.

Reference:
Patent; Tianjin Normal University; SONG, FANBO; ZHANG, ZHONGBIAO; LI, HUAYUN; TANG, HONGYING; WANG, ZHIQIANG; SONG, AIRU; (11 pag.)CN104004016; (2016); B;,
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These common heterocyclic compound, 612-24-8, name is 2-Nitrobenzonitrile, 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. 612-24-8

General procedure: A round bottom flask equipped with a magnetic stirrer bar was charged with the 2-nitroacylbenzene (1.00 mmol) in EtOAc-MeOH (1:1; 5 mL). SnCl2.H2O (3.00 mmol) was added and the reaction stirred at room temperature overnight. The reaction was partitioned between DCM (30 mL) and NaHCO3 (20 mL). The aqueous phase was extracted with DCM (3 ¡Á 10 mL) and the organic portions combined, washed with H2O (10 mL), saturated aqueous NaCl (10 mL), dried over MgSO4, filtered and reduced in vacuo. The residue was purified by column chromatography (SiO2, hexane/EtOAc) to provide the title compound. General procedure gave the title compound as an orange solid (116 mg, 87 %).

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 612-24-8.

Reference:
Article; Chauhan, Jay; Fletcher, Steven; Tetrahedron Letters; vol. 53; 37; (2012); p. 4951 – 4954;,
Nitrile – Wikipedia,
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27387-23-1, name is 2-(2-Bromo-5-methoxyphenyl)acetonitrile, 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. 27387-23-1

D. N, N-DIMETHYL-5-METHOXY-2-BROMOPHENYLACETAMIDE 5-Methoxy-2-bromobenzoic acid (85 g, 0.37 mol) is dissolved in anhydrous THF (100 mL) and cooled in an ice-salt bath until the temperature REACHES-5 C. Borane-THF complex is added dropwise as a 1.0 M solution in THF (736 mL, 0.74 mol) AT-5C. After addition is complete, the reaction mixture is slowly warmed to room temperature and stirred for 12 hours. Water (40 mL) is slowly added dropwise and the reaction mixture stirred for 30 minutes. Additional water (350 mL) is added and the mixture is concentrated by rotary evaporator to remove most of the THF. The remaining material is extracted with EtOAc (800 mL). The organic layer is washed with saturated NAHCO3 (500 mL), brine (250 mL) and then dried (NA2SO4). UPON REMOVAL of the solvent by rotary evaporator, 5-methoxy-2- bromobenzyl alcohol is obtained as a white solid. 5-Methoxy-2-bromobenzyl alcohol (79.5 g, 0.37 mol) is dissolved in 48% HBr (400 mL) and heated to reflux temperature for 4 hours. The reaction mixture is cooled to room temperature and poured into water (1500 mL). The solution is extracted with EtOAc (2 x 500 mL). The combined organic layers are dried (MGS04) and concentrated by rotary evaporator. The crude material is then purified using flash chromatography (CH2CI2/hexanes, from 1: 1 to 4: 1) to give 5-methoxy-2-bromobenzyl bromide. 5-METHOXY-2-BROMOBENZYL bromide (72.8 g, 0.26 mol) is dissolved in EtOH (280 mL) and stirred at room temperature. Sodium cyanide (38.2 g, 0.78 mol) is dissolved in water and added to the solution of the bromide. The reaction mixture is heated to reflux temperature for 3 hours and then cooled to room temperature. Most of the ethanol is removed by rotary evaporator. A solid forms which is isolated by filtration and washed with water (500 mL). The crude material is purified using flash chromatography (CH2CI2/HEXANES, 1: 1) to give 5-methoxy-2-bromophenylacetonitrile (53 g). 5-Methoxy-2-bromophenylacetonitrile (52.8 g, 0.23 mol) is dissolved in ethanol (250 mL) and stirred at room temperature. Sodium hydroxide (9.3 g, 0.47 mol) is dissolved in water (150 mL) and added to the solution of the nitrile. The mixture is heated to reflux temperature for 12 hours and then cooled to room temperature. Most of the ethanol is removed using a rotary evaporator and the residual aqueous solution adjusted to pH 4 with 3 N HCI. The solid which forms is isolated by filtration and washed with water. Air drying gives 5-methoxy-2-bromophenylacetic acid. 5-Methoxy-2-bromophenylacetic acid (56 g, 0.23 mol) is dissolved in CH2CI2 (350 mL) and a catalytic amount of DMF is added and the solution stirred and cooled to 0C. Thionyl chloride (41 mL, 0.34 mol) is added dropwise. The reaction mixture is heated at reflux temperature overnight and then cooled to room temperature. Solvents are removed by rotary evaporator. Twice benzene (500 mL) is added to the residual oil and the benzene solution is evaporated by rotary evaporator to remove any additional volatile components. The residual oil is crystallized from hexanes to give 5-methoxy-2-bromophenylacetyl chloride. 5-Methoxy-2-bromophenylacetyl chloride (60 g, 0.23 mol) is dissolved in anhydrous ET20 (400 mL), stirred and cooled in an ice bath. A 2 M solution of DIMETHYLAMINE (228 mL, 0.46 mol) is added dropwise and the mixture allowed to warm to room temperature and stirred for 2 hours. Additional ET20 (500 mL) is added. The organic solution is washed with 1 N HCI (2 x 500 mL), saturated NAHCO3 (500 mL) and brine (500 mL). The organic layer is dried (NA2SO4) and concentrated by rotary evaporator. The residue is purified using flash chromatography (hexanes/EtOAc, from 7: 3 to 1: 9). Trituration of the crude product with ET20/HEXANES gives N, N-DIMETHYL-5-METHOXY-2-BROMOPHENYLACETAMIDE AS a white crystalline solid (m. p. 88-90C).

Statistics shows that 27387-23-1 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromo-5-methoxyphenyl)acetonitrile.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/48314; (2004); A1;,
Nitrile – Wikipedia,
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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. 151-18-8 name is 3-Aminopropanenitrile, 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. 151-18-8

To a suspension of (S)-3-(5-benzylisoxazole-3-carboxamido)-5-methyl-4-oxo- 2,3,4,5-tetrahydrobenzo [b][l,4]oxazepine-7-carboxylic acid (87.0 mg, 0.206 mmol) in DCM (2.0 mL) was added l-chloro-N,N,2-trimethylprop-l -en- 1 -amine (33.1 mg, 0.248 mmol) as a solution in DCM (0.10 ml) dropwise over 1 min. The reaction mixture was stirred at rt for lh and became a homogeneous solution. The reaction mixture was cooled in an ice-bath then 3-aminopropanenitrile (57.9 mg, 0.826 mmol) was added dropwise as a solution in DCM (0.25 mL). The ice-bath was removed then 10 % aq citric acid solution was added and the mixture was stirred vigorously for 15 min . The organic phase was separated, washed with sat. aq sodium bicarbonate and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by FCC( EtO Ac-Hex: 60-80%) to yield the desired product(67.0 mg, 68.5 %). MS (m/z) 474.4 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Aminopropanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); 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. 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 60899-34-5

PREPARATION 10 1-hydroxy-4-indanecarbonitrile (racemic) 1.46 g of 4-cyano-1-indanone in 131 ml of tetrahydrofuran is cooled to +5 C., 1 g of potassium borohydride is added in small fractions, with agitation for one hour 15 minutes, followed by pouring over 200 ml of water containing sodium chloride, and extraction with isopropyl ether. The organic phase is dried, brought to dryness under reduced pressure and the residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4). 1.40 g of expected product is obtained, M.p.=98 C.

The synthetic route of 60899-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roussel Uclaf; US5180741; (1993); A;,
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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. 127946-77-4 name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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. 127946-77-4

(3R,4R)-N-( 1 -Cyanocyclopropyl)-4-(5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)-2-(5 – fluoropyridin-3 -yl)thiazol-4-yl)bicyclo [4.1 . 0]heptane-3 -carboxamide was synthesized following the same procedure as in Step H of Example 1 using (3R,4R)-4-(5-(4-(1,1- dioxidothiomorpholino)phenyl)-2-(5 -fluoropyridin-3 -yl)thiazol-4-yl)bicyclo [4.1 . 0]heptane-3 -carboxylic acid (0.180 g, 0.340 mmol, 1.00 equiv), DMF (5 mL), 1- aminocyclopropanecarbonitrile hydrochloride (0.202 g, 1.70 mmol, 5.00 equiv), HATU (0.324 g, 0.850 mmol, 2.50 equiv) and DIPEA (0.330 g, 2.55 mmol, 7.48 equiv). This resulted in 0.135 g (67%) of (3R,4R)-N-( 1 -Cyanocyclopropyl)-4-(5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)-2-(5 – fluoropyridin-3-yl)thiazol-4-yl)bicyclo[4. 1 .0]heptane-3-carboxamide as a yellow solid: MS (ES,m/z): 592.1 (M + 1).

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:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
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4426-11-3, A common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

Example 163A 1-cyclopentylcyclobutanecarbonitrile To a solution of cyclobutanecarbonitrile (405 mg, 5 mmol) in THF (7 mL) was added dropwise LDA (2.0 M, 2.5 mL, 5 mmol) at -78 C. over 10 minutes. After stirring for 30 minutes, a solution ofbromocyclopentane (888 mg, 6.0 mmol) in HMPA (268 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with the addition of 1N aqueous HCl (10 mL) and extracted with EtOAc (20 mL*3). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (petroleum ether/EtOAc=20/1) to give Example 163A (0.46 g, yield 62.3%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 2.53-2.44 (m, 2H), 2.25-2.07 (m, 4H), 2.03-1.95 (m, 1H), 1.86-1.69 (m, 4H), 1.62-1.54 (m, 2H).

The synthetic route of Cyclobutanecarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Nitrile – Wikipedia,
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215800-25-2, These common heterocyclic compound, 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile, 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 d intermediate 472-(4-bromo-3-methylphenyl)-2-methylpropanenitrileTo a stirred solution of 2-(4-bromo-3-methylphenyl)acetonitrile (11.2 g, 53.3 mmol) in anhydrous DMF (125 mL) is added methyl iodide (13.2 mL, 213 mmol). The solution is cooled to O0C and sodium hydride (60% susp. in oil, 3.84 g, 160 mmol) is added in small portions over 20 min. The reaction mixture is then left stirring and slowly warmed up to room temperature for 18 h. At O0C, water (500 mL) is then slowly added then extracted with ethyl acetate containing 10% of hexanes. The organic layer is separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-3-methylphenyl)-2- methylpropanenitrile (12.6 g, 99 %) as a clear yellow oil which is used in the next step without further purification. IH NMR (400 MHz, CHLOROFORM-D) 5 ppm 1.71 (s, 6 H) 2.43 (s, 3 H) 7.14 (dd, /=8.40, 2.34 Hz, 1 H) 7.34 (d, /=2.54 Hz, 1 H) 7.53 (d, /=8.40 Hz, 1 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 215800-25-2.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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A common compound: 4110-35-4, name is 3,5-Dinitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4110-35-4

Example 137Alternative Preparation of 3-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)-5-nitrobenzonitrileA mixture of 3,5-dinitrobenzonitrile (386 mg, 2.0 mmol), 1-methyl-1H-tetrazol-5(4H)-one (400 mg, 4.0 mmol) and K2CO3 (552 mg, 4.0 mmol) in NMP (6 mL) was heated to 110 C. and stirred overnight. After allowing to cool, the mixture was poured in to H2O (75 mL) and EtOAc (40 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (2¡Á30 mL). The combined organic extracts were washed with brine (1¡Á20 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc/hexane (3:7 to 4:6) as eluent to give the product (182 mg, 37%) as a solid.Data identical to previously synthesized material. (Example 136)Note: 1-methyl-1H-tetrazol-5(4H)-one was prepared according to procedure detailed in EP643049 (1995); Preparation of 1-substituted-5(4H)-tetrazolinones by desulfurization of tetrazolinethiones, which is hereby incorporated by reference.

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, 4110-35-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha; US2011/130415; (2011); A1;,
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2941-29-9, name is Cyclopentanone-2-carbonitrile, 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. 2941-29-9

To a solution of intermediate 15-e ( 1.8 g, 6.01 mmol) in toluene (30.0 ml), was added 2-oxocyclopentanecarbonitrile (984 mg, 9.02 mmol) and 4- methylbenzenesulfonic acid hydrate ( 114 mg, 0.60 mmol) . The reaction was refluxed for 3 hours using a dean-stark and then cooled to room temperature. Saturated aqueous NaHC03 and ethyl acetate were added, the organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 15-f as beige solid . MS (m/z) M + H= 391.5

Statistics shows that 2941-29-9 is playing an increasingly important role. we look forward to future research findings about Cyclopentanone-2-carbonitrile.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; MORRIS, Stephen; JAQUITH, James; WO2012/135937; (2012); A1;,
Nitrile – Wikipedia,
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