Tag: M.W=200-300

Synthetic Route of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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.

(0527) To a stirred suspension of (R)-4-phenyloxazolidin-2-one (100 mg, 0.613 mmol), 4- bromo-2,5-difluorobenzonitrile (134 mg, 0.613 mmol), copper(I) iodide (175 mg, 0.919 mmol), and potassium carbonate (254 mg, 1.84 mmol) in anhydrous 1,4-dioxane (3.0 mL) under an atmosphere of nitrogen was added (1S,2S)-(+)-N,N’-dimethylcyclohexane-1,2-diamine (0.29 mL, 1.8 mmol) and the resulting mixture was heated at 90 C for 20 h. After cooling to ambient temperature the mixture was filtered through a pad of Celite and the filtered solids were washed with ethyl acetate (30 mL). The combined filtrates were evaporated to dryness in vacuo and the crude residue was purified by flash silica gel chromatography (ISCO CombiFlash Rf Purification System; 12 g SepaFlash Silica Flash Column, eluting with a 0-50% ethyl acetate in hexanes gradient) to afford the title compound as an oil. MS (ESI) m/z [M+H+CH3CN]+: 342.2.

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; WANG, Deping; FRALEY, Mark, E.; JONES, Kristen, G.; (273 pag.)WO2017/222951; (2017); A1;,
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Reference of 70484-02-5,Some common heterocyclic compound, 70484-02-5, name is 6-Bromonaphthalene-2,3-dicarbonitrile, molecular formula is C12H5BrN2, 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.

SYNTHESIS EXAMPLE 15 Synthesis of 6-cyclohexylthio-2,3-dicyanonaphthalene Ten grams (38.9 mmoles) of 6-bromo-2,3-dicyanonaphthalene and 14 g (77.9 mmoles) of copper cyclohexylthiolate STR135 were refluxed in a mixed solvent of 200 ml of quinoline and 55 ml of pyridine for 20 hours until the starting compounds had completely been consumed. After cooling, the reaction mixture was poured into 1/1 mixture of water and methanol, and the deposited precipitate was collected by filtration. After separating decomposed products and by-products present in the crystal thus obtained by silica gel column chromatography, it was recrystallized from toluene/hexane to obtain 7.33 g (63%) of a light yellow crystal. Referring to the following analyses, it was identified as 6-cyclohexylthio-2,3-dicyanonaphthalene.

The synthetic route of 70484-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hitachi, Ltd.; Hitachi Chemical Co., Ltd.; US5484685; (1996); A;,
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Reference of 1217-45-4,Some common heterocyclic compound, 1217-45-4, name is 9,10-Anthracenedicarbonitrile, molecular formula is C16H8N2, 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 99 STR107 (+-)-Cis-3,4,9,9a-tetrahydroindeno[2,1-c]thiopyran-4a(1H)-amine To a solution of the benzylamine (1.0 g, 3.4 mmol) from Example 98 in acetonitrile/water (7:3) is added 9,10-dicyanoanthracene. The reaction is irradiated as described in Tetrahedron Letters 29, 4157 (1988). The reaction yields the primary amine which is converted to the title compound.

The synthetic route of 1217-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bigge; Christopher F.; Hays; Sheryl J.; Johnson; Graham; Novak; Perry M.; Ortwine; Daniel F.; US5071853; (1991); A;,
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Adding a certain compound to certain chemical reactions, such as: 70484-02-5, name is 6-Bromonaphthalene-2,3-dicarbonitrile, 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 70484-02-5, COA of Formula: C12H5BrN2

A mixture of 6-Bromodicyanonaphthalene(3) (1.0 g, 3.9 mmol), methyl-p-hydroxybenzoate (4)(2.0g, 13.2 mmol) and 6 g of K2CO3 in dry DMF (60 mL) was heated at 130for 20 h. After cooling down, the mixture was poured into ice water and extracted with chloroform, and then was washed with water thoroughly. The organic phase was dried over anhydrous MgSO4and concentrated, which was chromatographed (silica gel) usingCHCl3/ethyl acetate (40:1) as the eluent to give 5 as a white solid (0.28 g, 22%). 1H NMR (300 MHz, CDCl3, 25C, TMS): (ppm): 3.94 (s, 3H, CH3), 7.14 (d, 2H, Ar-H, J = 8.7), 7.38 (d, 1H, Ar-H, J=2.4 Hz), 7.56 (dd, 1H, Ar-H, J1=2.4 Hz, J2=9.0 Hz), 8.0 (d, 1H,Ar-H, J=9.0 Hz),8.12 (d, 2H, Ar-H, J=8.7 Hz), 8.18 (s, 1H, Ar-H), 8.33 (s, 1H, Ar-H). 13C NMR(75MHz, CDCl3, 25C, TMS): (ppm): 52.25, 108.96, 111.14, 114.03, 115.69, 115.84, 119.39, 124.29, 126.87, 129.80, 131.09, 132.14, 134.67, 134.75, 135.57, 158.54, 159.15, 166.17. MS (ESI) m/z 329.09; (M+H+) (calculated for 329.32).

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Reference:
Article; Luan, Liqiang; Ding, Lanlan; Zhang, Weijia; Shi, Jiawei; Yu, Xiaoqiang; Liu, Wei; Bioorganic and Medicinal Chemistry Letters; vol. 23; 13; (2013); p. 3775 – 3779;,
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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. 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8BrNO2

STEP 1 : To a pressure vessel were added ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), cesium carbonate (1.28 g, 3.94 mmol), pentan-3 -amine (688 uL, 5.90 mmol), XANTPHOS (1 14 mg, 0.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (90 mg, 0.10 mmol), and dioxane (3 mL). The vessel was sealed and heated to 95 C for 15 h. After cooling to room temperature, the mixture was filtered through celite and the filter cake rinsed with ethyl acetate. The filtrate was then concentrated and the residue was purified by column chromatography (10% ethyl acetate in hexanes) to provide ethyl 4-cyano-3- (pentan-3-ylamino)benzoate (315 mg, 1.21 mmol, 61% yield) as a yellow syrup. 1H NMR (400 MHz, CDCl3): 7.43 (d, IH), 7.33 (s, I H), 7.25 (dd, IH), 4.44-4.35 (m, 3H), 3.48-3.40 (m ,1H), 1..72-1.48 (m ,4H), 1.40 (t, 3H), 0.96 (t, 6H); MS (EI) for Ci5H20N2O2: 261 (MH+).

The synthetic route of 362527-61-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, 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 362527-61-5, Recommanded Product: 362527-61-5

EXAMPLE 206A 3-bromo-4-cyanobenzoic acid A solution of Example 87C (150 mg) in methanol (3 mL) and water (1 mL) was treated with LiOH (80 mg) and stirred for 2 hours. The solution was adjusted to pH 2 with 1M HCl, then extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. MS (DCI/NH3) m/z 243 and 245 (M+NH4)+; 1H NMR (300 MHz, CDCl3) delta 8.40 (d, 1H), 8.13 (dd, 1H), 7.79 (d, 1H).

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Reference:
Patent; Wang, Wei-Bo; Curtin, Michael L.; Fakhoury, Stephen A.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Hutchins, Charles W.; Li, Qun; Lin, Nan-Horng; Nelson, Lissa Taka Jennings; O’Connor, Steve; Sham, Hing L.; Sullivan, Gerard M.; Wang, Gary T.; Wang, Xilu; US2002/19527; (2002); A1;,
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Application of 916792-09-1,Some common heterocyclic compound, 916792-09-1, name is 2-Bromo-4-fluoro-6-methylbenzonitrile, 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.

2-Bromo-4-fluoro-6-methyl-benzonitrile (IX) (0.428 g, 2 mmol) was heated in 70% aqueous sulfuric acid (2 mL)overnight at 150 00 The reaction mixture was poured into ice and extracted with ethyl acetate (4 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried over Na2SO4, filtered and concentrated to give 300 mg of crude 2-bromo-4-fluoro-6-methyl-benzamide (VIII). Pure sample was obtained by recrystallization from benzene. 1H NMR (400.5 MHz, DMSO-d6) ppm 3.31 (s, 3H), 7.17 (dd, JH-F = 9.8 Hz, JH-H 2.2 Hz, 1H), 7.41 (dd, JH-F 8.6Hz, JH-H = 2.2 Hz, 1H), 7.89 (br. s, 1H), 7.65 (br. s, 1H).

The synthetic route of 916792-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PAPEO, Gianluca Mariano Enrico; KRASAVIN, Mikhail Yurievitch; ORSINI, Paolo; SCOLARO, Alessandra; WO2014/64149; (2014); A1;,
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Synthetic Route of 35764-15-9, These common heterocyclic compound, 35764-15-9, name is 2-Bromo-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.

Into a 5 mL microwave vial were charged methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (300 mg, 0.85 mmol), 2-bromo-4- (trifluoromethyl)benzonitrile (425 mg, 1.70 mmol), cesium carbonate (1.38 g, 4.25 mmol), tetra-n- butylammonium iodide (314 mg, 0.85 mmol), POPd (43 mg, 0.085 mmol), water (0.6 mL) and NN- dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150 0C for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to afford the residue which was purified by silica gel column to yield the title compound.

The synthetic route of 35764-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WEI, Zhi-Liang; GOWLUGARI, Sumithra; KAUB, Carl; WANG, Zhan; CAO, Yeyu; KINCAID, John; WO2010/33168; (2010); A2;,
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Synthetic Route of 32446-66-5,Some common heterocyclic compound, 32446-66-5, name is 4,4′-Dicyanobenzophenone, molecular formula is C15H8N2O, 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.

4-[(4-Cyanophenyl)methanehydrazonoyl]benzonitrile (8u). To a mixture of 4-[(4- eyanophenyl)earbonyl]benzonitrile (6u) (0.56 g, 2.4 mmol) and EtOH (30 ml) hydrazine monohydrate (1.8 g, 36 mmol) was added dropwise over 5 mm. The yellow solution wasstirred overnight (about 16 h) at 80C, the mixture was allowed to cool to rt and EtOAe (150 ml) was added. The organic layer was washed with water (50 ml + 2 x 25 ml). The inorganic wash layers were extracted with EtOAe (2 x 25 ml). The organic layers were combined, washed neutral with aq. sat. NaC1 (25 ml), dried over Na2SO4 and concentrated at reduced pressure to afford a slightly red solid 8u (0.51 g, 86%).

The synthetic route of 32446-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); 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. 57381-39-2, name is 2-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-5-fluorobenzonitrile

A suspension of [2-BROMO-5-FLUOROBENZONITRILE] (30.0 g, 150 mmol), bis (pinacolato) diboron (41.9 g, 165 mmol) and potassium acetate (29.4 g, 300 mmol) in 1,4-dioxane (375 ml) and DMSO (30 ml) was degassed with nitrogen for 1 h. Dichloro [[L,] [1′-BIS] (diphenylphosphino) ferrocene]- palladium (II) dichloromethane adduct (3.7 g, 4.5 mmol) was added and the mixture heated at [90C] for [18] h. The mixture was allowed to cool to ambient temperature then diluted with diethyl ether (300 ml) and filtered through a glass microfibre filter paper. The solvent was evaporated and the residue was treated with ice-cold 2N sodium hydroxide solution (250 ml) and the mixture left to stir for 15 min. The aqueous phase was extracted with diethyl ether (200 ml). The pH of the aqueous was adjusted to 5 by the addition of concentrated hydrochloric acid. The aqueous phase was extracted with diethyl ether (2 x 200 ml), the organic phase was combined, washed with water (150 ml) and brine (150 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give 5-fluoro-2- (4,4, 5, [5-TETRAMETHYL- [1,] 3,2] dioxaborolan-2-yl) benzonitrile (36.5 g, [98%)] as a brown oil which crystallised on standing: [5H] (360 MHz, CDCl3) 1.38 (12H, s), 7.25-7.30 (1H, m), 7.40 (1H, dd, J 3 and 8), 7.91 (1H, dd, J 6 and 8). 5-Fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)- benzonitrile (0.99 g, 4.0 mmol) and [1,] 3-dibromo-5-fluorobenzene (1.52 g, [6.] 0 mmol) were suspended in 1,2-dimethoxyethane (8 ml) and 2N sodium carbonate solution (4 [ML)] and degassed for 30 min before addition of tetrakis (triphenylphosphine) palladium [(0).] On complete addition the mixture was heated at [65C] for 20 h. The mixture was partitioned between ethyl acetate (100 ml) and water (50 ml), the organic layer separated and washed with brine (50 ml), dried over anhydrous sodium sulphate, filtered and evaporated onto silica. The product was purified by flash column chromatography on silica, eluting with isohexane on a gradient of diethyl ether (5-100%). Combination of the desired fractions and evaporation gave [3′-BROMO-4,] [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (110 mg, 9%) as a white solid: [SN] (500 MHz, [CD13)] 7.53-7. 55 [(1H,] m), 7.67 (1H, s), 7.69-7. 76 (3H, m), 8.03 [(1H,] dd, [J 9 AND] 2). [2- (8-FLUOROIMIDAZO [L,] 2-a] [PYRIDIN-7-YL)] propan-2-ol (58 mg, 0.3 mmol) and 3′-bromo-4, [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (106 mg, 0.36 mmol) were coupled following the procedure in Example 6 to afford 4,3′-difluoro- 5′- [8-fluoro-7- (l-hydroxy-l-methylethyl) imidazo [1, [2-A] PYRIDIN-3-YL]-] [BIPHENYL-2-CARBONITRILE] (25 mg, 20%) as a white solid: [SN] (500 MHz, [CD13)] 1.74 (6H, s), 2.07 [(1H,] s), 7.22-7. 26 (2H, m), 7.35 [(1H,] d, J 9), 7.39-7. 45 [(1H,] m), 7.51-7. 57 (3H, m), 7.76 [(1H,] s), 8.35 [(1H,] d, J 7) ; [RNLZ] (ES+) 408 (100%, [[MH] +).]

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 57381-39-2.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99816; (2003); A1;,
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