Water → 2-Chloro-6-oxetan-3-yl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 1799549Notes

Reaction equation

HRID 1799549 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]Cl)[C:5]([C:10]([O:12]C)=O)=[CH:4][CH:3]=1.Cl.[O:15]1[CH2:18][CH:17]([NH2:19])[CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][N:19]([CH:17]3[CH2:18][O:15][CH2:16]3)[C:10](=[O:12])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23062080Oxetan-3-amine hydrochlorideHCID 59525762Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

Product 1

HCID 582166452-Chloro-6-oxetan-3-yl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate (Example 1, Step 4) (0.15 g, 0.68 mmol), oxetan-3-amine hydrochloride (0.15 g, 1.36 mmol) and potassium carbonate (0.38 g, 2.7 mmol) were stirred in DMF (10 mL) at room temperature overnight. Water and ethyl acetate were added and the biphasic mixture was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (6-50% EtOAc/hexanes) gave the title compound as a white solid.

Workup

  1. extractionthe biphasic mixture was extracted with ethyl acetate (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel chromatography (6-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9bf3e3d7ab684127889daae7ee77b3d4
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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