Methanol → HCID 11502380, compound

Participants

Reaction Conditions

Reaction Steps

Bring bisazaindole 19 (48 mg, 0.0856 mmol) to reflux in KOH at 3%/MeOH for 8 h, then continue heating at 55° C. for 16 h. The reaction medium is then concentrated under vacuum, the residue is diluted with EtOAc, washed with saturated NaHCO3, dried (MgSO4), and concentrated until a residual oil is obtained. The latter is submitted to flash chromatography to give 20 (19.7 mg, 56.6%) as a white solid: 1H NMR (CDCl3) δ 10.77 (s broad, 1H), 8.20 (d, 1H, J=4.5 Hz), 7.82 (d, 1H, J=7.5 Hz), 7.57 (s, 1H), 7.13 (s, 1H), 7.03 (m, 1H), 6.57 (d, 1H, J=1.5 Hz), 4.23 (s, 3H), 4.22 (t, 2H, J=6.6 Hz), 3.96 (s, 3H), 3.70 (t, 4H, J=4.6 Hz), 2.77 (t, 2H, J=6.4 Hz), 2.49 (t, 4H, J=4.6 Hz). TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.20, m/z obs.=408.26 (M+1).

Provenance & Evidence