1H-Pyrrolo(2,3-b)pyridine → HCID 67171743, compound

HRID 450109Notes

Reaction equation

HRID 450109 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[C:12]([N:19]1[CH2:24][CH2:23][CH2:22][C:21](=O)C1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>CO.O>[NH:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[C:3]([C:22]2[CH2:21][N:19]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:24][CH:23]=2)=[CH:2]1.[NH:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[C:3]([C:23]2[CH2:22][CH2:21][N:19]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH:24]=2)=[CH:2]1

Participants

7

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 2

HCID 67171743HCID 67171743, compoundHCID 67172412HCID 67172412, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 7-azaindole (2.6 g, 22.0 mmol) in MeOH (120 mL) and water (60 mL) was added KOH (12.35 g) and the mixture was heated to 75° C. N-Boc-piperidin-3-one (20.4 g, 110 mmol) in methanol was added dropwise and following completion of the addition the mixture was stirred at 75° C. overnight. The reaction mixture was concentrated in vacuo, and the residue was taken up in water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulphate and concentrated to dryness. The residue was purified by column chromatography (DCM/MeOH) to afford tert-butyl 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (1 g) and tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate (1 g).

Workup

  1. additioncompletion of the addition the mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-f6b52fe3a6ac49939b663f032522aefb
Source dataset
uspto-grants-2013_07
Patent number
US08486964B2

Reaction notes

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