Related Products of 1914-02-9, 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. 1914-02-9 name is 3,3-Dimethylindoline, 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.
A mixture of 3,3-dimethylindoline (105 mg, 0.713 mmol), ethyl 2-bromo-2-cyclopropylacetate (297 muL, 2.143 mmol), and potassium carbonate (300 mg, 2.171 mmol) in 2 mL CH3CN was stirred at 100C (oil bath) for 16 h. The mixture was extracted with 2 M HC1 and CH2C12. Organic phases were concentrated and residue was purified by preparative HPLC. Fractions containing product were partly concentrated and the residue was extracted with 1 M NaHC03and CH2C12. Organic phases were dried over MgS04, filtered, and concentrate to give ethyl 2-cyclopropyl-2-(3,3-dimethylindolin-l-yl)acetate (162 mg) as a brownish oil. LCMS m/z = 274.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 0.37-0.43 (m, 1H), 0.52-0.58 (m, 1H), 0.61-0.73 (m, 2H), 1.20 (t, J = 7.1 Hz, 3H), 1.26-1.34 (m, 7H), 3.33 (d, J = 9.4 Hz, 1H), 3.49 (d, J = 8.4 Hz, 1H), 3.61 (d, J = 8.4 Hz, 1H), 4.13 (q, J = 7.1 Hz, 2H), 6.30 (dd, J1= 7.5 Hz, J2= 0.8 Hz, 1H), 6.63-6.67 (m, 1H), 6.98-7.02 (m, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dimethylindoline, and friends who are interested can also refer to it.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem