1H-Pyrrolo(2,3-b)pyridine → HCID 86610503, compound

HRID 1754690Notes

Reaction equation

HRID 1754690 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Br:10][C:11]1[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1.[OH-].[K+]>CO>[Br:10][C:11]1[N:16]=[CH:15][C:14]([CH:17]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[OH:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86610503HCID 86610503, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1H-Pyrrolo[2,3-b]pyridine (1, 1.2 g, 0.010 mol), 6-bromo-pyridine-3-carbaldehyde (88, 1.8 g, 0.0097 mol), and potassium hydroxide (1.8 g, 0.032 mol) in methanol (25 mL) was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the compound as a white solid (89, 1.4 g, 45%), or may be used as mixture of 89 and 90 in Step 2.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-ce89eed928444f3795f06b0508552659
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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