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

HRID 2277617Notes

Reaction equation

HRID 2277617 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:22])([CH3:21])[N:9](CC3C=CC(OC)=CC=3)[C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1.O.CCOC(C)=O>CC#N>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:22])([CH3:21])[NH:9][C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 866859402-Chloro-6,7-dihydro-6-[(4-methoxyphenyl)methyl]-7,7-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 717438192-Chloro-7,7-dimethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To solution of 2-chloro-6-(4-methoxy-benzyl)-7,7-dimethyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (1.58 g, 5.0 mmol) in CH3CN (20 mL) was added ceric ammonium nitrate (8.2 g, 15.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours before water and EtOAc was added into the mixture. The organic layer was separated, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by silica gel column chromatography to give title compound (617 mg, 63%) as a solid. MS: 197.2 (M+H+).

Workup

  1. additionwas added into the mixture
  2. customThe organic layer was separated
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43b52c0b9ed143d087796ff469f8d504
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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