Water → HCID 91583876, compound

Participants

Reaction Steps

To a solution of Example 40D (100 mg, 0.22 mmol) in CH3CN (1.0 mL) was added K2CO3 (150 mg, 1.1 mmol) and bromomethyl acetate (20 μL, 0.22 mmol). The reaction solution was heated to reflux with stirring for 2 hours, cooled, diluted with ethyl acetate and poured into water. The organics were separated, dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by reverse phase HPLC (water:acetonitrile; gradient of 5% to 90% acetonitrile) to provide the title compound (23 mg, 0.054 mmol, 24%). MS (ESI APCI) m/z 419.19 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ 8.01 (s, 1H) 7.37 (d, J=8.82 Hz, 2H) 7.04 (d, J=9.19 Hz, 2H) 4.57-4.72 (m, 2H) 3.83 (bs, 2H) 3.66 (s, 3H) 1.57 (d, J=6.99 Hz, 3H) 1.29 (d, J=6.25 Hz, 6H).

Provenance & Evidence