Month: June 2021

Related Products of 63069-50-1, These common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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.

A 50% aqueous solution of Hydroxylamine (2.18 mL, 33.1 mmol) was added to a 2-propanol (44 mL) solution of 4-amino-3-fluorobenzonitrile (3.00 g, 22.0 mmol) at room temperature, and the mixture was stirred at 70C for 5 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was washed with a hexane-ethyl acetate (4:1, v/v) mixture to give the title compound (3.67 g, yield: 98%). 1H-NMR (500 MHz, DMSO-d6) delta ppm: 9.35 (1H, s), 7.27 (1H, dd, J = 13, 2 Hz), 7.21 (1H, dd, J = 8, 2 Hz), 6.71 (1H, dd, J = 9, 8 Hz), 5.63 (2H, s), 5.33 (2H, s).

The synthetic route of 63069-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; YAMANOI, Shigeo; NAMIKI, Hidenori; OCHIAI, Yuichi; HOSHINO, Madoka; MATSUMOTO, Koji; EP2805941; (2014); 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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-4-methylbenzonitrile

2,6-Difluoro-N-[2′-methyl-5′-(4-methyl-thiazol-2-yl)-biphenyl-4-yl]-benzamide A solution of 3-bromo-4-methyl-benzonitrile (500 mg, 2.55 mmol) in ammonia solution (2 M in ethanol, 10 mL) was bubbled with H2S gas slowly for 1 hr. The solution was stirred for 3 hr at room temperature before the nitrogen was bubbled through the solution to remove H2S. The solution was concentrated to give the crude s (450 mg) which was used directly in the next reaction. The solution of s (100 mg, 0.43 mmol) and 1-chloropropan-2-one (200 muL, 2.5 mmol) in ethanol (2 mL) was refluxed at 85 C. for 10 hr. The solvent was removed and column chromatography afforded t (60 mg, 52%). Compound 38 was obtained by a Suzuki coupling reaction analogous to that described for Compound 20. 1H NMR (300 MHz, CDCl3) delta 7.93 (s, 1H), 7.80-7.68 (m, 4H), 7.40-7.29 (m, 4H), 7.03-6.96 (m, 2H), 6.82 (s, 1H), 2.48 (s, 3H), 2.31 (s, 3H); ESMS cacld (C24H18F2N2OS): 420.1; found: 421.1 (M+H).

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; Synta Pharmaceuticals Corp.; US2006/173006; (2006); A1;,
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Reference of 1483-54-1, 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. 1483-54-1 name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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.

General procedure: In a 50 mL round bottom flask, a suspension of 2-aminoarylnitriles (10.0 mmol) in ethyl chloroformate(52.0 mmol, 5.0 mL) was refluxing for 6 h. After complete removal of excess ethyl chloroformate in vacuo (by forming azeotrope with toluene), the residue was recrystallized from cyclohexane (for mostsubstrates) to furnish the title compound.

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

Reference:
Article; Nguyen, Huy H.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.; Tetrahedron Letters; vol. 56; 40; (2015); p. 5429 – 5433;,
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Reference of 60702-69-4, A common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

To a freshly-prepared solution of LDA (33.7 mmol) in anhydrous THF (30 mL) at -78Cwas added a solution of commercially available 2-chloro-4-fluorobenzonitrile (5.00 g,32.1 mmol) in THF (10 mL), dropwise at such a rate that the internal temperature remained < -70 C. The mixture was stirred for 2 h and a solution of iodine (8.97 g, 35.4 mmol) in THE (20 mL) was added dropwise (temp < -70 C). The mixture was stirred 30 min, removed from the cooling bath and quenched by addition of 10% Na2S2O3. Themixture was poured into water and extracted with EtOAc (x3). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in a small amount of CH2Cl2 and filtered through a pad of silica (25% EtOAc/hexanes eluent). Fractions containing the major product were concentrated in vacuo and the residue was recrystallized from heptane affording 3.24 g tan solid. Themother liquor was concentrated and the residue was purified by flash chromatography (EtOAc / hexanes, gradient elution) affording 2.85 g of a pale yellow solid. Solids were combined to give 2-chloro-4-fluoro-3-iodobenzonitrile (6.09 g, 67 % yield): 1H NMR (400MHz, CDCl3) delta 7.70 (dd, J = 8.6, 5.5 Hz, 1 H), 7.08 (dd, J = 8.6, 6.8 Hz, 1 H); MS (GCMS EI) m/z 281 ([M]+, 100%). The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; TURNBULL, Philip, Stewart; CADILLA, Rodolfo; WO2014/13309; (2014); A1;,
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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. 3100-67-2, name is 1-Amino-2-naphthonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Amino-2-naphthonitrile

A 2 L reactor was charged with 45.0 g (232 mmol) of intermediate 3-a, 450 mL of tetrahydrofuran was added thereto and stirred. after cooling to 0 C, 3M-phenylmagnesium bromide (88.2 mL, 487 mmol) was added dropwise, and refluxed for 3 hours. after cooling to 0 C, 44.3 g (732 mmol) of ethyl chloroformate was dissolved in 200 mL of tetrahydrofuran, and the mixture was refluxed for 2 hours. after cooling to 0 C, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 46.0 g (yield: 80.0%) of a compound represented by [Intermediate 3-b].

According to the analysis of related databases, 3100-67-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SFC Co.,Ltd; Sin, Bong Gi; Park, Ji Hee; Park, Boo Bae; Park, Gyung Hwa; (46 pag.)KR2016/36162; (2016); A;,
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Related Products of 26391-06-0,Some common heterocyclic compound, 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, molecular formula is C7H12N2O, 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.

Under a nitrogen atmosphere, 60% NaH (0.35g, 8.8 mmol) was added to solution of 2-cyano-N,N-diethylacetamide (0.56 g, 4.0 mmol) in anhydrous THF (15 mL) at -5 C. The resulting suspension was stirred at-S C for 15mm and the THF solution of 3,4-dimethoxy-5- nitrobenzoyl chloride was added over 10mm and stirred for an additional lh at -5C. The reaction mixture was warmed to 0 C, quenched by the addition of 1N.HC1 solution (4 mL) and stirred for 10mm at room temperature, extracted by ethyl acetate (25 mL X 2), the organic layers was dried with Na2504 and concentrated in vacuo to give the title compound as an orange solid (705 mg, 99%). MS [MH] calcd for C,6H,9N306 350.1, found 350.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Cyano-N,N-diethylacetamide, its application will become more common.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; HUANG, Niu; PENG, Shiming; (87 pag.)WO2016/206573; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, 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 115661-37-5, Recommanded Product: 2-Amino-3-fluorobenzonitrile

2-Amino-3-fluorobenzonitrile 45a (1 g, 7.35 mmol, purchased from Shanghai Bide Pharmatech Ltd.) was dissolved in 50 mL of dichloromethane. The reaction solution was added with N-bromosuccinimide (1.37 g, 7.71 mmol), and stirred for 16 hours. The reaction solution was added with water, and extracted with dichloromethane (50 mL×3). The organic phases were combined, washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 45b (1.25 g), yield: 79.13%. MS m/z (ESI):215.0 [M+1].

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; Jiangsu Hengrui Medicine Co. Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; LU, Biao; ZHANG, Junzhen; JIN, Fangfang; HE, Feng; TAO, Weikang; EP3569596; (2019); A1;,
Nitrile – Wikipedia,
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621-03-4, name is 2-Cyano-N-phenylacetamide, 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. Formula: C9H8N2O

General procedure: A mixture of beta-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.

The synthetic route of 621-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Zhengwang; Liu, Jiayang; Jin, Caiju; Tan, Qi; Ye, Min; Tetrahedron Letters; vol. 60; 18; (2019); p. 1265 – 1267;,
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Application of 60899-34-5, 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. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, 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.

To 1-oxo-2,3-dihydro-JH-indene-4-carbonitrile INT-1 (42.5 g, 0.27 mol) and (R)-2-methylpropane-2-sulfinamide (36.0 g, 0.30 mol) in toluene (530 mL)was added titanium tetraethoxide (84.1 mL, 92.5 g, 0.40 mol) and the reaction mixture was heated at 60C for 12 h under N2. The crude (R)-N-(4-cyano-2,3-dihydro-1H- indene-1-ylidene)-2-methylpropane-2-sulfinamide INT-4 was used directly in the next experiment. LCMS-ESI (m/z) calculated for C14H16N20S: 260.3; found 261.1 [M+H],3.19 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; SCOTT, Fiona, Lorraine; MEADOWS, Kristen, R., Taylor; PEACH, Robert; (154 pag.)WO2018/64356; (2018); 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. 19472-74-3, name is 2-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 19472-74-3

To a solution of compound 5a (500 mg, 2.12 mmol) and 2-Bromophenylacetonitrile (538 mg, 2.76 mmol) in TMEDA (3 mL) and H2O (0.1 mL) was added Na2PdCl4 (6.23 mg, 0.02 mmol), CuI (7.62 mg, 0.04mmol) and 2-(Di-tert-butylphosphino)-1-phenylindole (13.5 mg, 0.04mmol). Under Ar, the mixture was warmed to 80 C and stirred for 3 h. After the mixture was cooled to warm temperature, water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 462 mg of compound 6 (yield: 62%) as a colorless liquid. 1H NMR (400 MHz, CDCl3): delta 7.50 – 7.44 (m, 2H), 7.38 (td, 1H, J = 7.6, 1.3 Hz), 7.30 (t, 1H, J = 7.5 Hz), 7.15 (t, 1H, J = 8.7 Hz), 6.78 – 6.70 (m, 2H), 4.93 (s, 2H), 3.72 (s, 3H), 3.79 (s, 2H), 2.95 – 2.89 (m, 2H), 2.60 (t, 2H, J = 7.6 Hz). MS (EI) m/z: 351 (M+).

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:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts