Imidazole → HCID 178456842, compound

Participants

Reaction Steps

To a solution of 2-(2-Isopropylamino-thiazol-4-yl)-quinoline-4,7-diol (1.27 g, 4.2 mmol) in 4 mL of DMF was added TIPSCl (2.67 mL, 12.6 mmol) followed by imidazole (2.86 g, 42 mmol). The solution was stirred for 5 min at rt, dissolved in 20 mL EtOAC, quenched by saturated solution of NH4Cl in H2O. The solution was extracted and evaporated under vacuo. The crude product was purified by silica gel chromatography using SiO2 (eluted with 5% to 20% MeOH/DCM) to give 2-(2-Isopropylamino-thiazol-4-yl)-7-triisopropylsilanyloxy-quinolin-4-ol as a dark orange solid (1.9 g, 99%). 1H-NMR (300 MHz, DMSO): δ 11.0 (bs, 1H), 7.93 (d, 1H), 7.70 (bs, 1H), 7.42 (s, 1H), 7.25 (s, 1H), 6.81 (dd, 1H), 6.49 (s, 1H), 3.97-3.87 (m, 1H), 1.38-1.25 (m, 1H), 1.22 (d, 6H), 1.07 (d, 6H).

Provenance & Evidence