Category: 362527-61-5

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., Application In Synthesis of Ethyl 3-bromo-4-cyanobenzoate

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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, Application In Synthesis of Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), XANTPHOS (228 mg, 0.39 mmol), cesium carbonate (1.282 g, 3.94 mmol), cyclopentylamine (233 mg, 2.75 mmol), and tris(dibenzylideneacetone)dipalladium (180 mg, 0.20 mmol) in dioxane (5 mL) was stirred at 1000C for 17 h. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL), the organic layer washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes: ethyl acetate 9: 1) afforded ethyl 4-cyano-3-(cyclopentylamino)benzoate (366 mg, 72% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): 7.43 (m, 2H), 7.35 (m, IH), 7.27 (m, IH), 4.62 (d, IH), 4.38 (q, 2H), 3.93 (m, IH), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.53 (m, 2H),1.39 (t, 3H). MS (EI) for Ci5H18N2O2: 259 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-bromo-4-cyanobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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, name: Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 2.08 mmol), 2-methylpropan-l -amine (250 muL, 4.16 mmol), Pd2(dba)3 (96 mg, 5 mol%), Xantphos (120 mg, 10 mol%) and potassium phosphate (959 mg, 4.16 mmol) in dioxane (10 mL) was stirred for overnight at 95 0C. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated followed by column chromatography (10 % ethyl acetate in hexanes) to give ethyl 4- cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 76.7 %) as a yellow solid. ‘ MS(EI) for C14H18N2O2: 247.1 (MH+).

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 3-bromo-4-cyanobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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, COA of Formula: C10H8BrNO2

EXAMPLE 2; Preparation of 3-Bromo-4-cyanobenzoic acid; A solution of ethyl 4-amino-3-bromobenzoate (23.5 g, 96.3 mmol) in methylene chloride at -10 C. is treated dropwise with tert-butyl nitrite (14.0 mL, 118.4 mmol), followed by boron trifluoride diethyl etherate (18.4 mL, 146.5 mmol). The reaction mixture is allowed to come to room temperature, stirred for 4 h, diluted with ethyl ether and filtered. The filtercake is dried, dispersed in toluene, cooled to 0 C., treated with a solution of copper (I) cyanide (11.5 g, 129.2 mmol) and sodium cyanide (15.8 g, 323.1 mmol) in water, stirred at 0 C. for 30 min., warmed to 60 C., stirred for 1 h, cooled to room temperature and diluted with EtOAc and water. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether/hexanes to give the ethyl ester of the title compound as an off-white solid, 18.6 g (76% yield). A solution of this ester (8.5 g, 33.6 mmol) in THF is treated with a solution of NaOH (30 mL, 2.5 N) and ethanol, stirred for 20 h, acidified with 2N HCl and extracted with ethyl ether. The ether extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether/hexanes to afford the title compound as a beige solid, 6.81 g (90% yield), identified by HNMR and mass spectral analyses. MS m/e 223 (M-H)+; 1H NMR (400 MHz, DMSO-d6) delta 8.05 (dd, J=9.76, 1.37 Hz 1 H), 8.09 (d, J=8.08 Hz, 1H), 8.29 (d, J=1.37 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-bromo-4-cyanobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/282825; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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).

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; 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts