Acetic Anhydride → 5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine

HRID 581234

Reaction equation

HRID 581234 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]2[CH:11]=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[K+].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C(OC(=O)C)(=O)C>CO>[C:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH:19]=3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 196015015-(N-acetylamino)pyrrolo[3,2-b]pyridine

Product 1

HCID 99035405-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.477 gm (2.7 mMol) of the 5-(N-acetylamino)pyrrolo[3,2-b]pyridine, 0.54 mg (9.5 mMol) potassium hydroxide, and 0.43 mL (3.5 mMol) 1-methyl-4-piperidone in 15 mL methanol was heated at reflux for 18 hours. The reaction mixture was then concentrated under reduced pressure and the residue dissolved in pyridine. To this solution was added 0.20 mL (2.2 mMol) acetic anhydride and the resultant mixture stirred for 1 hour. This reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of ethyl acetate (2-40% methanol). Fractions containing product were combined and concentrated under reduced pressure to provide 0.43 gm (59%) 5-(N-acetylamino)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine as an ivory foam. A portion was recrystallized from methanol/ethyl acetate to provide an analytical sample.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. dissolutionthe residue dissolved in pyridine
  4. concentrationThis reaction mixture was concentrated under reduced pressure
  5. washeluting with a gradient of ethyl acetate (2-40% methanol)
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cda9e0edf02402882f40edfcf401c99
Source dataset
uspto-grants-1999_07
Patent number
US05919936

Linked notes

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