Formic Acid → HCID 136383517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 74G (10 mg, 0.016 mmol) in dichloroethane (0.1 mL) was added formic acid (1.2 μL, 0.032 mmol) followed by addition of aqueous 37% formaldehyde solution (1.3 μL, 0.018 mmol). The mixture was heated at 50° C. for 2 h. After cooling to room temperature, the solution was diluted with ethyl acetate (1 mL), washed with water (0.5 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (2% methanol/dichloromethane) afforded a greenish brown solid (6 mg, 60%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.31-0.50 (m, 1H), 0.73 (s, 9H), 0.90-1.07 (m, 1H), 2.11-2.30 (m, 1H), 2.35-2.48 (m, 1H), 2.71 (s, 3H), 3.00-3.10 (m, 3H), 3.45-3.62 (m, 1H), 4.07 (d, J=12.87 Hz, 1H), 7.26-7.40 (m, 5H), 7.42-7.60 (m, 3H), 7.64 (t, J=7.54 Hz, 1H), 7.71-7.80 (m, 1H), 7.93 (d, J=8.09 Hz, 1H), 8.22 (d, J=6.62 Hz, 1H), 10.06 (s, 1H), 13.53 (s, 1H); MS m/z 637.2 (M+H)+.

Provenance & Evidence