Reference of 64248-64-2, 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. 64248-64-2 name is 2,5-Difluorobenzonitrile, 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.
To a solution of (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (33 mg, 0.101 mmol) and 2,5-difluorobenzonitrile (18 mg, 0.129 mmol) in 0.5 mL THF, 1 M potassium teri-butoxide (0.150 mL, 0.150 mmol) was added slowly. After stirring at room temperature for 1 h, mixture was extracted with water and CH2C12. Organic phases were concentrated and residue was purified by HPLC (H20/CH3CN gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-(2-cyano-4-fluorophenoxy)cyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (37.9 mg, 85.26 muiotaetaomicron?, 84.1%) as a white solid. Exact mass calculated for C25H33FN204: 444.2, found: LCMS m/z = 445.6 [M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.41-1.69 (m, 8H), 1.47 (s, 9H), 1.87-2.10 (m, 8H), 3.50-3.56 (m, 1H), 3.77-3.85 (m, 1H), 4.16-4.31 (m, 2H), 4.33-4.39 (m, 1H), 6.92-7.00 (m, 1H), 7.20-7.26 (m, 2.4 Hz, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Difluorobenzonitrile, and friends who are interested can also refer to it.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts