Trifluoroacetic acid → 2-(4-Tert-butyl-phenyl)-4-fluoro-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one

HRID 2251857Notes

Reaction equation

HRID 2251857 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:19](O)[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([F:21])[C:13]=3[C:12]2=[O:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:19][C:18]3[CH:17]=[CH:16][N:15]=[C:14]([F:21])[C:13]=3[C:12]2=[O:22])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 690319892-(4-Tert-butyl-phenyl)-4-fluoro-1-hydroxy-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one

Product 1

HCID 690324422-(4-Tert-butyl-phenyl)-4-fluoro-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-tert-butyl-phenyl)-4-fluoro-1-hydroxy-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one (0.085 g, 0.28 mmol, Step C) and triethylsilane (0.029 mL, 1.80 mmol) in 6 mL of CH2Cl2 was added TFA (0.62 mL, 7.80 mmol) at RT. The mixture was heated at reflux for 2 h, and the volatiles were removed under reduced pressure. The residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2), to yield the titled compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customthe volatiles were removed under reduced pressure
  4. customThe residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-2343a2b58e6e46f5af47403ce9b4ba28
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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