Methanol → 1H-Pyrrolo[3,2-b]pyridine, 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dimethoxy-1-methyl-

HRID 506783Notes

Reaction equation

HRID 506783 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]([CH3:24])[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]([CH3:24])[CH:12]=3)=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 887MethanolHCID 46868293HCID 46868293, compound

Product 1

HCID 116387311H-Pyrrolo[3,2-b]pyridine, 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dimethoxy-1-methyl-

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Reflux bisazaindole 29 (40 mg, 0.081 mmol) in KOH at 4%/MeOH (10 mL) for 5.5 h and then concentrate the reaction under vacuum. Purification on SiO2 (MeOH at 2-4%/CH2Cl2) leads to 30 (13 mg, 47.3%) as a white solid: 1H NMR (CDCl3) δ 10.92 (s broad, 1H), 8.07 (d, 1H, J=5.3 Hz), 7.49 (s, 1H), 7.05 (s apparent overlapping d, 2H, J=5.2 Hz), 6.62 (s, 1H), 4.22 (s, 3H), 3.96 (s, 3H), 3.81 (s, 3H), TLC (EtOAc at 40%/heptane), Rf=0.40, m/z obs.=343.3 (M+1), 345.3.

Workup

  1. concentrationconcentrate
  2. customthe reaction under vacuum
  3. customPurification on SiO2 (MeOH at 2-4%/CH2Cl2)

Sources & evidence

ORD record
ord-147da80550794cf8a39d5b9c68ab7f1f
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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