Water → N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Participants

Reaction Steps

N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)benzamide (2E, 1.9 g, 1.0 equivalent) was dissolved in THF (0.4 M). Cooled mixture in ice bath, and followed by a slow addition of TBAF (1.0M THF solution, 6.5 equivalents). After addition, mixture was warmed to room temperature and then heated to 60° C. for 3 h. After stirring, water was added and followed by extraction with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 1 to 5% MeOH/CH2Cl2) to give 2F (60%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6H) 3.48 (s, 2H) 4.77 (br. s., 1H) 7.57 (d, J=8.59 Hz, 2H) 7.72 (d, J=8.34 Hz, 1H) 8.05-8.16 (m, 3H) 13.08 (s, 1H); ESI-MS: m/z 406.0 (M+H)+.

Provenance & Evidence