Potassium Hydroxide → HCID 11546710, compound

HRID 506787Notes

Reaction equation

HRID 506787 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]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 46868294HCID 46868294, compound

Product 1

HCID 11546710HCID 11546710, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. temperaturereflux for 16 h
  2. concentrationConcentrate the reaction medium under vacuum
  3. washThe organic phase is washed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-ffa2b833ce8d4a028bf2703a67af8d15
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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