Sodium Iodide → HCID 90046968, compound

Participants

Reaction Steps

To a solution of 6-(tert-butylsulfonyl)-4-chloroquinolin-7-ol (250 mg, 0.834 mmol) in DMF (2756 μl) was added K2CO3 (576 mg, 4.17 mmol) followed by 1-chloro-2-methylpropan-2-ol (209 μl, 2.502 mmol). After 10 min, LCMS showed no product. Heated reaction to 60° C. No reaction after 3 hr at this temperature. Added sodium iodide (375 mg, 2.50 mmol) and 2,2-dimethyloxirane (371 μl, 4.17 mmol) and stirred for 2 days at to 60° C. The crude sample was purified via Biotage normal phase chromatography (25 g SNAP column, 0% -80%, 80%. hex/EtOAc). The pure product containing-fractions were combined and concentrated leading to the product as an off-white solid: 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)-2-methylpropan-2-ol (46 mg, 0.124 mmol, 14.83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (s, 6H) 1.33 (s, 9H) 4.03 (s, 2H) 4.56 (s, 1H) 7.72 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.64 (s, 1H) 8.94 (d, J=4.80 Hz, 1H). MS (m/z) 372.2 (M+H+).

Provenance & Evidence