Sodium Methoxide → HCID 86685942, compound

HRID 2277619Notes

Reaction equation

HRID 2277619 reaction equation
Cl[C:2]1[N:7]=[C:6]2[C:8]([CH3:22])([CH3:21])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1.[CH3:23][O-:24].[Na+]>CN(C=O)C>[CH3:23][O:24][C:2]1[N:7]=[C:6]2[C:8]([CH3:22])([CH3:21])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866859402-Chloro-6,7-dihydro-6-[(4-methoxyphenyl)methyl]-7,7-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 86685942HCID 86685942, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-chloro-6-(4-methoxy-benzyl)-7,7-dimethyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (intermediate A-16 [F], 3.15 g, 10 mmol) in DMF (30 mL) was added sodium methanolate (0.813 g, 15 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 hours before it was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give title compound (2.8 g, 90%) as a solid. MS: 313.1 (M+H+).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4baf95915c764fa8b442cf6f7a49434b
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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