Methanol → HCID 11590590, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[N:13]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12.CO>[OH-].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[N:13]([CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]4)[CH:12]=3)=[CH:10][C:3]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Reflux bisazaindole 35 (40 mg, 0.066 mmol) in KOH at 3%/MeOH (10 mL) for 16 h, then concentrate under vacuum. The residue is dissolved in EtOAc, washed with saturated NaHCO3, dried (Na2SO4) and submitted to flash chromatography on SiO2 (MeOH at 4%/CH2Cl2, 0.25% of NH3) to give 36 (18 mg, 60.2%) as a white solid: 1H NMR (CDCl3. δ 10.94 (s broad, 1H), 8.07 (d, 1H, J=5.2 Hz), 7.61 (s, 1H), 7.15 (s, 1H), 7.05 (d, 1H, J=5.2 Hz), 6.65 (d, 1H, J=2 Hz), 4.23 (s overlapping t, 5H, J=6.5 Hz), 3.97 (s, 3H), 2.79 (t, 2H, J=6.5 Hz), 2.55-2.45 (m broad, 8H), 2.29 (s, 3H), TLC (MeOH at 10%/CH2Cl2, 0.25% of NH3) Rf=0.35, m/z obs.=455.11 (M+1).