Tag: M.W=200-300

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Sodium hydride (168 mg, 7.02 mmol, 1.0 eq. ) was added to a solution of 6, 6-dimethyl-3-trifluoromethyl-1, 5, 6, 7- tetrahydro-indazol-4-one (1.63 g, 7.02 mmol, 1.0 eq. ) in 35 mL of anhydrous dimethyl sulfoxide. After 15 min 2-bromo-4- fluorobenzonitrile (2.25 g, 11.23 mmol, 1.6 eq. ) was added as a solid. The reaction mixture was heated at 45 0C. After 23 h the reaction mixture was cooled to ambient temperature and quenched with 10 mL of saturated aqueous ammonium chloride. The mixture was diluted with water and extracted with ethyl acetate (4x) . The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on a Biotage (SiO2, hexanes-ethyl acetate) to afford 2-bromo-4- (6, 6-dimethyl-4- oxo-3-trifluoromethyl-4, 5,6, 7-tetrahydro-indazol-l-yl) – benzonitrile (1.83 g, 63%) as an off-white powder, LC/MS: (M+H) = 412.0.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4592-94-3, These common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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.

General procedure: To a stirred solution of 3-oxo-3-aryl-propionitriles 2 and Et3N (0.101 g, 1 mmol) inCH3OH:H2O (2:1, 6 mL) was added adducts of acenaphthoquinone and malononitrile or ethylcycnoacetate 1 (1 mmol) at room temperature. After completion of the reaction [about 30-120min, TLC (n-hexan/EtOAc, 2:1) monitoring], the solvent was evaporated under vacuum and thecrude product was purified by flash column chromatography on silica gel using EtOAc/n-hexane(1:2) as eluent (for compound 3a-d) and or was washed by methanol (for compounds 3e-h) toafford the pure product 3.

Statistics shows that 3-(4-Bromophenyl)-3-oxopropanenitrile is playing an increasingly important role. we look forward to future research findings about 4592-94-3.

Reference:
Article; Yavari, Issa; Khajeh-Khezri, Aliyeh; Bahemmat, Samira; Halvagar, Mohammad Reza; Synlett; vol. 28; 14; (2017); p. 1785 – 1788;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 330793-38-9,Some common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, molecular formula is C8H6BrNO, 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.

General procedure: Following general procedure Q, 4-bromo-2-methoxybenzonitrile (108 mg, 0.51 mmol) gave (4-bromo- 2-methoxy-phenyl)methanamine (67.2 mg, 0.31 mmol, 61 percent yield). NMR (500 MHz, CDCI3, delta): 7.12-7.02 (m, 2H), 7.00-6.96 (m, 1 H), 3.84 (s, 3H), 3.77 (s, 2H). To a solution of cobalt (II) chloride (1 eq.) and nitrile derivative (1 eq.) in anhydrous MeOH (0.05 M), cooled to 0 ¡ãC under a nitrogen atmosphere, was added sodium borohydride (10 eq) portion wise over 10 min. The reaction mixture was then stirred for 20 min at 0 ¡ãC and then stirred for a further 60 min at room temperature, quenched with an aqueous solution of ammonium chloride, and allowed to stand overnight. Most of methanol was removed under reduced pressure and the remaining aqueous mixture was diluted with water and washed with Epsilon2theta (x 2). The aqueous layer was basified to pH = 12 with 1 M NaOH and extracted with CHC (* 3). The combined organics were dried (phase separator) and concentrated to give the desired amine.

The synthetic route of 330793-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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. HPLC of Formula: C8H3ClF3N

General procedure: Appropriate ROH (3.00 mmol) was added topotassium tert-butoxide (3.00 mmol) solution in toluene (7 ml).1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 3ml)was added to the mixture and stirred for 30 min at 80 C. Aftercooled down to ambient temperature of the reaction mixture,2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) in toluenewas dropwise and stirred for 3 h at 80 C. The reaction wasquenched by adding water and extracted with EtOAc twice. Thecombined organic extracts were dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:7) eluantcondition.

The synthetic route of 2-Chloro-4-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 69316-08-1, name is Methyl 4-(cyanoacetyl)benzoate, molecular formula is C11H9NO3, 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. Product Details of 69316-08-1

4-(5-Amino-2H-pyrazol-3-yl)-benzoic acid methyl ester The named compound is the 3-aminopyrazole used in the reaction of Example 23 and can be prepared from commercially available 4-(2-cyano-acetyl)-benzoic acid methyl ester by the following method: 4-(2-Cyano-acetyl)-benzoic acid methyl ester (1.0 gm.) is dissolved in 9.29 mL anydrous EtOH, treated with anhydrous hydrazine (0.37 mL) and heated to reflux. The resulting reaction mixture is refluxed for 24 h, subsequently cooled to room temperature, and concentrated in vacuo to provide the named compound in the amount of 0.45 gms.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 69316-08-1, its application will become more common.

Reference:
Patent; Allergan, Inc.; US6559173; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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 13338-63-1, 13338-63-1

Using the method of synthesizing an intermediate similar to that of Example 1,Take 0.01 mol of 3,4,5-trimethoxyphenylacetonitrile (5), 0.01 mol of 4-trifluoromethylbenzaldehyde and 20 mL of methanol into a 50 mL three-necked flask.Stirring to 60 C, adding 0.005 mol of sodium methoxide, constant temperature reaction 4-6 h,TLC scanning and detection, after the reaction is completed, it is cooled to room temperature, filtered, washed with water, dried, and recrystallized from methanol to obtain a pale yellow solid. Yield: 38.6%,

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, 3,4,5-Trimethoxyphenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yanbian University; Bu Gonggaofamingren; (14 pag.)CN108503561; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

13338-63-1, These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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.

General procedure: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16].

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 13338-63-1.

Reference:
Article; Madadi, Nikhil R.; Penthala, Narsimha R.; Howk, Kevin; Ketkar, Amit; Eoff, Robert L.; Borrelli, Michael J.; Crooks, Peter A.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 123 – 132;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts