HCID 100304374, compound → HCID 118108318, compound

Participants

Reaction Steps

2-Methyl-5-propoxyindole-3-carboxaldehyde 409b (200 mg, 0.920 mmol) was reacted in a similar manner to that for 402a to yield a bright yellow powder (204 mg, 69%): mp 228-229° C. TLC Rf 0.40 (80% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.88 (s, 1H), 8.81-8.80 (m, 2H), 8.08-8.06 (d, 1H, J=15.3 Hz), 7.93-7.92 (m, 2H), 7.41 (d, 1H, J=2.22 Hz), 7.34-7.31 (d, 1H, J=15.24 Hz), 7.30-7.29 (d, 1H, J=8.64 Hz), 6.85-6.83 (dd, 1H, J1=8.64 Hz, J2=2.28 Hz), 4.04-4.02 (t, 2H, 6.54 Hz), 2.56 (s, 3H), 1.80-1.74 (sex, 2H, J=6.66 Hz), 1.03-1.01 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, d6-DMSO) δ 188.2, 154.6, 150.6, 145.75, 145.18, 139.6, 131.0, 126.6, 121.4, 112.90, 112.25, 111.4, 109.3, 104.4, 69.6, 22.3, 12.2, 10.6. Elemental analysis calculated for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 75.00; H, 6.23; N, 8.69.

Provenance & Evidence