Dimethylformamide → HCID 68233580, compound

Participants

Reaction Steps

To a solution of compound 15 (40 mg, 0.1 mmol) in DMF (3 mL) at 0° C. was added NaH (168 mg, 0.4 mmol). The mixture was stirred at rt for 0.5 h and to it was added MeI (22 mg, 0.16 mmol). The reaction was stirred at rt for 2.5 h, quenched with H2O and extracted with EA (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give compound 16 (22 mg, 53% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 8.51 (d, 1H, J=8.0 Hz), 8.16 (d, 1H, J=8.0 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.60 (t, 1H, J=8.0 Hz), 7.46-7.43 (m, 1H), 7.18 (d, 1H, J=8.0 Hz), 7.00 (d, 1H, J=7.6 Hz), 6.91-6.82 (m, 2H), 5.12 (d, 1H, J=8.0 Hz), 4.99-4.90 (m, 2H), 4.72 (s, 1H), 4.62-4.59 (d, 1H), 4.23 (d, 1H, J=8.0 Hz), 3.76 (d, 1H, J=8.8 Hz), 3.60 (t, 1H, J=8.0 Hz), 3.33-3.29 (m, 1H), 3.17 (s, 3H). MS (ESI) calcd for [C21H22N2O4S+H]+ (m/z): 399.48. found: 399.2.

Provenance & Evidence