Sodium ethoxide → HCID 86685943, compound

HRID 2277621Notes

Reaction equation

HRID 2277621 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.[O-:23][CH2:24][CH3:25].[Na+]>CN(C=O)C>[CH2:24]([O:23][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)[CH3:25]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 866859402-Chloro-6,7-dihydro-6-[(4-methoxyphenyl)methyl]-7,7-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 86685943HCID 86685943, compoundYield 89%

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 ethoxide (1.02 g, 15 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 hours before it was quenched by water and extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give title product (2.9 g, 89%) as a solid. MS: 327.2 (M+H+).

Workup

  1. customwas quenched by 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-1498fc7e5a9a40f6a16f0968236f5b22
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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