Synthesis
GENERAL PROCEDURE: To a solution of 2-carboxylic acid-5-bromopyridine (200 mg, 1 mmol) in dichloromethane (5 mL) was slowly added thionyl chloride (1 mL) dropwise and a drop of N,N-dimethylformamide (DMF). The reaction mixture was heated to 80 °C and maintained for 1 hour. Upon completion of the reaction, it was cooled to room temperature, the reaction mixture was concentrated and the residue was dissolved in dichloromethane (2 mL). The resulting solution was slowly added dropwise to ammonia (3 mL) at room temperature. Subsequently, the mixture was stirred at room temperature for 1.5 hours. At the end of the reaction, the mixture was concentrated to give 5-bromopyridinecarboxamide (85 mg, 92.4% yield) as a white solid. Liquid mass spectrometry (electrospray ionization) m/z ([M+H]+) measured value 201.2; calculated value 201.0.
References
[1] Patent: WO2014/81619, 2014, A1. Location in patent: Page/Page column 46
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4860 - 4882
[3] Patent: US2006/217387, 2006, A1. Location in patent: Page/Page column 31
[4] Patent: WO2012/76063, 2012, A1. Location in patent: Page/Page column 39
[5] Patent: US2013/261100, 2013, A1. Location in patent: Paragraph 0279-0280
