Uses
2-(2-Chloropyridin-3-yl)acetic Acid can be prepared to use as RORγ agonists for the treatment of cancer.
Synthesis
General procedure for the synthesis of 2-chloropyridine-3-acetic acid from (2-chloropyridin-3-yl)acetonitrile: 15% w/w NaOH solution (15 mL) was added to (2-chloropyridin-3-yl)acetonitrile (0.932 g, 6.1 mmol). The reaction mixture was heated to reflux for 35 min and subsequently cooled to room temperature. The mixture was further cooled to 0 °C and acidified to pH 1 with concentrated hydrochloric acid (about 5 mL of hydrochloric acid was required). The resulting suspension was allowed to stand in an ice bath for 1 hour. The precipitate was collected by filtration and washed with cold isopropanol (3 x 15 mL) to afford 2-chloropyridine-3-acetic acid (1.05 g, 100% yield) as an off-white solid.1H NMR (400 MHz, d6-DMSO) δ 12.63 (s, 1H), 8.32 (dd, J = 4.8, 1.9 Hz, 1H), 7.86 (dd, J = 7.5, 1.9 Hz, 1H). 1.9 Hz, 1H), 7.41 (dd, J = 7.5, 4.8 Hz, 1H), 3.75 (s, 2H).LCMS Method C: Retention time 4.06 min; m/z 172 [M+H]+.
References
[1] Patent: WO2012/110773, 2012, A1. Location in patent: Page/Page column 138; 139
[2] Patent: WO2014/27199, 2014, A1. Location in patent: Page/Page column 141
[3] Patent: WO2009/13462, 2009, A1. Location in patent: Page/Page column 26
[4] Patent: WO2009/93008, 2009, A1. Location in patent: Page/Page column 25-26
[5] Patent: WO2009/153554, 2009, A1. Location in patent: Page/Page column 36
