Water → HCID 68669139, compound

HRID 1964910Notes

Reaction equation

HRID 1964910 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)[CH:13]=1.[OH-].[K+].O>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]([C:26]2[C:20]3[C:21](=[N:22][CH:23]=[C:18]([C:14]4[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=4)[CH:19]=3)[NH:24][CH:25]=2)[OH:8])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 14797Potassium HydroxideHCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68669139HCID 68669139, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-nitrobenzaldehyde (534, 1.08 g, 7.17 mmol) in methanol (34 mL) was added 5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (89, 1.08 g, 5.52 mmol, prepared as described in Example 17) and potassium hydroxide (1.55 g, 27.6 mmol). The reaction was stirred at room temperature for four hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The mixture was purified by silica gel column chromatography eluting with 4% methanol in dichloromethane to provide two different compounds, a white solid (P-1399, R═H, 1.20 g, 63%) MS(ESI) [M+H+]+=347.2, and a light yellow solid (535, R=Me, 0.434 g, 22%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe mixture was purified by silica gel column chromatography
  6. washeluting with 4% methanol in dichloromethane
  7. customto provide two different compounds

Sources & evidence

ORD record
ord-2faa2f0bb80f4d909600f0eace015be2
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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