Tag: M.W=200-300

Electric Literature of 57381-37-0, 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. 57381-37-0 name is 2-Bromo-5-chlorobenzonitrile, 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 50 : (R)-4 ‘-( 4-Amino-8-methyl-5-oxo-7,8-dihvdropyrimido [5,4- f| [ 1 ,41 oxazepin-6( 5H)-yl)-4-chloro-2 ‘-fluor obiphenyl-2-carbonitrile; (i~)-4-Amino-6-(3-fluoro-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)phenyl)-8- methyl-7,8-dihydropyrimido[5,4-f][l ,4]oxazepin-5(6H)-one (Intermediate 51 ; 290 mg, 0.70 mmol), PdCl2(dppf)-DCM adduct (28.6 mg, 0.04 mmol), potassium phosphate (0.07 mL, 0.84 mmol) and 2-bromo-5-chlorobenzonitrile (182 mg, 0.84 mmol) were suspended in DME (3 mL), ethanol (1.5 mL) and water (0.75 mL) and sealed into a microwave tube, degassed under vacuum and the atmosphere replaced with nitrogen. The reaction was heated to 130 C for 90 minutes in the microwave reactor and cooled to RT. The reaction mixture was evaporated to dryness and redissolved in methyl THF (25 mL), and washed sequentially with water (25 mL) and saturated brine (25 mL). The organic layer was dried over Na2SC”4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC (Waters XBridge Prep CI 8 OBD column, 5mu silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (74.0 mg, 24.94 %) as a white solid. 1H NMR (400 MHz, CDC13, 30C) 2.61 (3H, s), 3.89 – 4.00 (2H, m), 4.86 – 5.08 (1H, m), 5.51 – 5.74 (1H, m), 7.22 (1H, d), 7.49 (2H, dd), 7.66 (1H, dd), 7.78 (1H, d), 7.82 – 8.07 (1H, m), 8.33 (1H, s). m/z (ES+), (M+H)+ = 424

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIRCH, Alan, Martin; GOLDBERG, Frederick, Woolf; LEACH, Andrew; WO2011/121350; (2011); A1;,
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Electric Literature of 52133-67-2, 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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Hydroxybenzamidine hydrochloride (15.2 g) was dissolved in absolute ethanol (520 ml.) and a part of the ethanol (370 ml.) was subsequently distilled off again. More absolute ethanol (370 ml.) was added to this receiving solution, together with DBU (30 ml_), 2-cyano-4,4-diethoxy-butyric acid ethyl ester (40.0 g) and triethyl amine (26 ml_). The resulting mixture was heated until reflux and further refluxed for 45 hours (“hrs”). Most of the solvent (430 ml.) was then distilled off while the remainder was allowed to cool to 50 0C. An aqueous solution of hydrochloric acid (2.3 M, 229 ml.) was added dropwise, then the reaction mixture was allowed to cool to ambient temperature and stirring was continued for 1 hr. The resulting precipitate was filtered off, washed with water (3 x 100 ml.) and dried in vacuo at 40 0C to yield 16.0 g 2-(4-hydroxy-phenyl)-7/-/-pyrrolo[2,3-d]pyrimidin-4-ol

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, Ethyl 2-cyano-4,4-diethoxybutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SOLVAY PHARMACEUTICALS GMBH; WO2009/153261; (2009); A1;,
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Application of 97165-77-0, 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 97165-77-0 as follows.

To a flask was added 3,5-dibromobenzonitrile (3 g, 11.6 mmol), 4-(1-naphthyl)-benzenesulfonic acid (2.9 g, 11.6 mmol), potassium carbonate (4.1 g, 30 mmol)tetraphenyllphosphine palladium (0.1 g),tetrahydrofuran (30 mL) and water (15 mL)heated to reflux under nitrogen for 12 hours, cooled, extracted with dichloromethane, dried and concentrated. The crude product was purified by column chromatography to give 2.5 g of product in 57% yield.

According to the analysis of related databases, 97165-77-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Daoyi Chemical Technology Co., Ltd.; Huang Jinhai; Su Jianhua; (29 pag.)CN107033143; (2017); A;,
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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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 3,4,5,6-Tetrafluorophthalonitrile

Example 2 When the reaction was performed by following the procedure of Example 1 while using 60 g (0.50 mol) of diethylene glycol monomethyl ether as the solvent for the cyclization in place of n-octanol, the amount of the target product, hexadecafluorovanadylphthalocyanine, was found to be 23.1 gr (yield: 71.1 mol percent).

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 1835-65-0.

Reference:
Patent; Hirota, Kouichi; Hashimoto, Yukihide; Masuda, Kiyoshi; Kitao, Masunori; US2005/203293; (2005); A1;,
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Application of 30041-95-3, These common heterocyclic compound, 30041-95-3, name is Ethyl 2-(4-cyanophenoxy)acetate, 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: B(C6F5)3 (67.3 mg, 0.13 mmol, 5 mol %) was added to a stirred solution of 3,4-dichlorobenzaldehyde (172 mg, 1 mmol) and NaN3 (97.5 mg, 1.5 mmol) in DMF (5 mL) and was heated at 120 C. After completion of reaction (as monitored by TLC), the reaction mixture was cooled to room temperature and was added 5 mL of cold water followed by 10 mL of 2 N HCl and 10 mL of ethyl acetate. The resulting mixture was stirred vigorously for 15 min. The organic layer was separated and aqueous layer was again extracted with ethyl acetate (3 ¡Á 15 mL). The combined organic layer was washed with water and dried over anhydrous sodium sulfate and was evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel, EtOAc/hexane 9:1) to obtain pure 5-(3,4-dichlorophenyl)-1H-tetrazole. The known compounds were characterized and confirmed by comparison of their spectral data and physical properties with reported literature.

Statistics shows that Ethyl 2-(4-cyanophenoxy)acetate is playing an increasingly important role. we look forward to future research findings about 30041-95-3.

Reference:
Article; Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Babu, Bathini Nagendra; Tetrahedron Letters; vol. 55; 24; (2014); p. 3507 – 3510;,
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Related Products of 120315-65-3, 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. 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-bromo-3-methoxybenzonitrile (1.4 g, 6.7 mmol), allyl-tributyl-stannane (2.7 g, 8.1 mmol), LiCl (0.86 mg, 20 mmol) and Pd(PPh)4 (0.2 g) in 25 mL of anhydrous toluene was refluxed under N2 overnight. Checked the reaction with TLC and concentrated under reduced pressure. The residue was purified by silica gel cloumn chromatography to give the product 4-allyl-3-methoxybenzonitrile. MS m/z: 174 (M+1)+.

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-Bromo-3-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; TANG, Haifeng; PASTERNAK, Alexander; YANG, Lihu; WALSH, Shawn, P.; PIO, Barbara; SHAHRIPOUR, Aurash; TEUMELSAN, Nardos; (111 pag.)EP2632465; (2015); B1;,
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Reference of 57381-49-4, A common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

[1,1′-bis(diphenylphosphino)dicene. Iron] Palladium dichloride (192.8 mg, 0.26 mmol) and potassium carbonate (1.09 g,7.91mmol) wereadded. The reaction mixture was heated to 110C and the reaction was stirred for 16 hours.The reaction solution was allowed to cool to room temperature and20 mL of water was addedto the reaction mixture. The mixture was extracted with ethyl acetate (20 mL ¡Á 3). The organic phases were combined and the organic phase was washed with saturated sodium chloride solution (20 mL ¡Á2) and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedby silica gel column chromatography using an eluent system C togive the crude title product 4d (450 mg, yellow viscous product), which was directly introduced into the next reaction.

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; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
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Application of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-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.

Example 7: 5-Brorno-N-l,3-thiazol-2-yl-lH-indazol-3-amne SCN[0275] Hydrazine monohydrate (2.6 mL, 52.5 mmol) was added to a solution of 5-bromo- 2-fluorobenzonitrile (3.50 g, 17.5 mmol) in ethanol (50 mL) at room temperature. The mixture was stirred for 4 h under reflux condition. After cooling, the mixture was diluted with EtOAc (300 mL), washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by recrystallization (EtOAc-hexane) gave 3.37g (91%) of 5-bromo- lH-indazol-3-amine (compound 7A) as a white solid. 1H NMR (300 MHz, CDCl3) delta 4.07 (brs, 2 H) 7.20 (d, IH77=8.85 Hz) 7.42 (dd, IH, J=8.85, 1.70 Hz) 7.71 (d, IH, 7=1.51 Hz) 8.98 (brs, 1 H). MS (ES) [m+H] calc’d for C7H6BrN^, 213; found 211, 213. [0276] Ammonium thiocyanate (229 mg, 3 mmol) was added to a suspension of 5-bromo- lH-indazol-3-amine (212 mg, 1 mmol) in IN hydrochloric acid (3 mL). The mixture was stirred for 4 days at 1000C. The precipitate was collected, and washed with eta2O to give 231 mg (85%) of N-(5-bromo-lH-indazol-3-yI)thiourea (compound 7B) as a yellow solid. 1H NMR (300 MHz, DMSO-rf6) delta 7.43 (d, IH, 7=8.85 Hz) 7.50 (dd, IH, 7=8.85, 1.88 Hz) 8.49 (d, IH, 7=1.32 Hz) 8.79 (brs, IH) 9.18 (brs, IH) 10.85 (s, IH) 12.86 (s, IH). MS (ES) [m+H] calc’d for C8H7BrN4S, 272; found 270, 272.[0277] To a stirred solution of N-(5-bromo-lH-indazol-3-yl)thiourea (104 mg, 0.38 mmol) in ethanol (2 mL) and H2O (1 mL) was added 1 ,2-dichloroethyl ethyl ether (0.05 mL, 0.41 mmol) at room temperature. The mixture was stirred for 3 h at 8O0C. After dilution with EtOAc, the organic layer was washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Crystallization from EtOAc-diisopropyl ether gave 62.7 mg (55%) of 5-Bromo-N-l,3-thiazol-2-yl-lH-indazol-3-amine (compound 7) as a white solid. 1H NMR (300 MHz, DMSO-^6) delta 7.01 (d, IH, 7=3.58 Hz) 7.36 (d, IH, 7=3.58 Hz) 7.37 – 7.42 (m, IH) 7.44 – 7.49 (m, IH) 8.35 (d, IH, 7=1.32 Hz) 11.34 (brs, IH) 12.53 (s, IH). MS (ES) [m+H] calc’d for C10H7BrN4S, 296; found 294, 296.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2007/75847; (2007); A2;,
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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. 236750-65-5, name is 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C13H16N2O6

(d) 2-amino-4, 5-bis (2-methoxyethoxy) benzonitrile:; To 4,5-bis (2-methoxyethoxy)-2-nitrobenzonitrile(10 g) was added acetic acid (75ml) and water(75ml), stirred the reaction mass for about 10 min, added Iron powder (7g) in portions over a period of 2hrs, Stirred the reaction mixture for about Vz hr at 300C adjusted PH of the reaction mass to 7. Extracted the material into ethylacetate, the organic layer was dried over sodium sulfate and concentrated to yield crystalline yellow solid. Which was further recrystallized from methanol (6g) mp 74-77 0C1HNMR (CDCI3): delta 3.43(s, 6H), 3.73(m, 4H), 4.08(m, 4H), 4.20(brs, 2H), 6.25(s, 1 H), 6.90(s, 1 H)

The synthetic route of 236750-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITTAL MALLYA SCIENTIFIC RESEARCH FOUNDATION; WO2007/138612; (2007); A2;; ; Patent; VITTAL MALLYA SCIENTIFIC RESEARCH FOUNDATION; WO2007/138613; (2007); A2;,
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Reference of 875664-25-8, 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. 875664-25-8, name is 4-Bromo-2-phenoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound 5c (35.3 g, 129 mmol) was added to 130 mL EtOH, followed by the addition of 340 ml_ of 20% aqueous NaOH. The reaction was heated to reflux for 20 h. At that time the mixture was cooled to room temperature and poured into 6 N HCI. The solid was collected by vacuum filtration, dissolved in 3:1 THF-ethyl ether, and washed with brine. The organic phase was dried (MgSO4) and concentrated. The solids were dried in a vacuum oven at 60C overnight to give the desired compound 1b. MS m/z (MH+) 292.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-phenoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/30089; (2007); A1;,
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