Isopropyl iodide → HCID 90386218, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-N-(tert-butyl)-2-hydroxypyridine-3-sulfonamide (1.50 g, 4.85 mmol) in DMF (40 mL) was added 2-iodopropane (0.825 g, 4.85 mmol) followed by K2CO3 (1.34 g, 9.70 mmol) at RT. The reaction mixture was heated to 100° C. for 14 h. The reaction mixture was allowed to cool and the volatile components were removed under reduced pressure. The residue was diluted with cold water (150 mL) and extracted into ethyl acetate (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure and the residue was purified by CombiFlash (REDISEP®, silica gel, 24 g, 50% EtOAc/petroleum ether) to give 5-bromo-N-(tert-butyl)-2-isopropoxypyridine-3-sulfonamide (0.660 g, 37.7%) as a white solid. LCMS Condition B-22: retention time 1.92 min, [M+1]=351.0. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.13 (s, 9H), 1.35 (d, J=6.8 Hz, 6H), 5.06 (dt, J=13.6 Hz, J=6.8 Hz, 1H), 6.96 (s, 1H), 8.00 (d, J=2.6 Hz, 1H), 8.36 (d, J=2.6 Hz, 1H).

Provenance & Evidence