Water → HCID 89884776, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of Example 1 (92 mg, 0.197 mmol) in DMF (10 mL) was cooled to 0° C. NaH (60%; 9 mg, 0.217 mmol) was added and the mixture was stirred at 0° C. for 5 minutes. Methyl iodide (30 mg, 0.207 mmol) was added and the mixture was stirred at r.t. for 16 h. Water (0.5 mL) was added and the mixture was evaporated in vacuo. The residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM, the combined organic fractions were washed with brine and dried Na2SO4), then the solvent was evaporated in vacuo. The residue was purified twice by column chromatography (SiO2, 0-35% MeOH in EtOAc) to give the title compound (16 mg, 17%) as an off-white solid. δH (DMSO-d6) 9.00 (d, J 1.7 Hz, 1H), 8.77 (dd, J 4.8, 1.6 Hz, 1H), 8.73-8.70 (m, 2H), 8.27 (dt, J 7.8, 1.8 Hz, 1H), 8.11 (dd, J 8.3, 1.2 Hz, 1H), 8.01 (s, 1H), 7.98 (dd, J 7.5, 1.2 Hz, 1H), 7.85 (dd, J 8.5, 1.2 Hz, 1H), 7.71 (dd, J 8.5, 4.4 Hz, 1H), 7.66-7.56 (m, 2H), 5.93 (q, J 7.7 Hz, 1H), 3.53 (s, 3H). LCMS (ES+) 481 (M+H)+, RT 2.31 minutes.

Provenance & Evidence