Potassium Hydroxide → HCID 11546710, 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][O:29][CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12.[OH-].[K+]>CO>[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][O:29][CH2:30][CH2:31]4)[CH:12]=3)=[CH:10][C:3]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Treat bisazaindole 33 (40 mg, 0.067 mmol) with KOH at 3%/MeOH (10 mL) and reflux for 16 h. Concentrate the reaction medium under vacuum and divide the residue between EtOAc and saturated NaHCO3. The organic phase is washed with saturated NaHCO3, dried (Na2SO4) and submitted to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2) to give 34 (19.0 mg, 64.2%) as a white solid: 1H NMR (CDCl3) δ 10.94 (s broad, 1H), 8.07 (d, 1H, J=5.0 Hz), 7.62 (s, 1H), 7.14 (s, 1H), 7.05 (d, 1H, J=5.3 Hz), 6.66 (d, 1H, J=1.9 Hz), 4.23 (s overlapping t, 5H, J=6.4 Hz), 3.97 (s, 3H), 3.70 (t, 4H, J=4.6 Hz), 2.79 (t, 2H, J=6.4 Hz), 2.50 (t, 4H, J=4.6 Hz), TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.25, m/z obs.=442.1 (M+1).