Extracurricular laboratory: Synthetic route of 60899-34-5

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 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.

(S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l-ylidene]-2-methylpropane-2- sulfinamide: To a solution of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in Toluene (60 mL) was added (S)-2-methylpropane-2-sulfinamide (4.24 g, 34.98 mmol, 1.10 equiv), Ti(OEt)4 (10.75 g, 47.15 mmol, 1.48 equiv). The resulting solution was stirred for 16 h at 60 C. The resulting solution was used directly in the next step without further purification. LC-MS: m/z = 261 [M+H]+. To a solution of l -oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in toluene (50 mL) was added (S)-2-methylpropane-2-sulfinamide (4.6 g, 37.95 mmol, 1.20 equiv), Ti(OEt)4 (1 1 g, 1.50 equiv). The resulting solution was stirred for 18 h at 60 C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of sat. potassium sodium tartrate (30 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 5.5 g (66%) of (S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l -ylidene]-2- methylpropane-2-sulfinamide as a yellow green solid. LC-MS: m/z = 261 [M+H]+.

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; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts