Acetic Anhydride → HCID 136396916, compound

Participants

Reaction Steps

To a solution of Example 26 (20 mg, 0.04 mmol) in dichloromethane (0.5 mL) was added triethylamine (17 μL, 0.12 mmol) and acetic anhydride (7 μL, 0.08 mmol) and the solution was stirred at room temperature for 16 hours. Solvent was removed in vacuo to yield bis-substituted material which is dissolved in methanol (2 mL) and solid K2CO3 (excess) was added and the solution stirred at room temperature for 1 hour. H2O (5 mL) was added and the solution extracted with ethyl acetate (3×5 mL). The combined extracts were washed with brine (1×5 mL), dried (Na2SO4), the drying agent filtered and the solvent removed in vacuo to give a crude residue which was purified by column chromatography on silica gel (3% methanol/chloroform) to give the title compound as a colorless solid. 1H NMR (d6-DMSO) δ 10.00 (s, 1H), 8.04, 8.01 (d, 1H), 7.57-7.33 (m, 6H), 3.02 (s, 3H), 1.91-1.79 (m, 1H), 1.82 (s, 3H), 1.72-1.62 (m, 1H), 1.31-1.13 (m, 2H), 0.89-0.63 (m, 2H), 0.72-0.63 (m, 3H). MS (ESI) m/z 547 (M+H+).

Provenance & Evidence