Trifluoroacetic acid → 4,7-Dichloro-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

HRID 21342Notes

Reaction equation

HRID 21342 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9](C(C)(C3C=CC=CC=3)C)[CH:10](O)[C:6]=2[C:5]([Cl:22])=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.CCCCCC.C(OCC)(=O)C>[N+](C)([O-])=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[NH:9][CH2:10][C:6]=2[C:5]([Cl:22])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21226206Ethyl acetate hexaneHCID 866283394,7-Dichloro-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

Product 1

HCID 768481314,7-Dichloro-1,2-dihydropyrrolo[3,4-c]pyridine-3-oneYield 72%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

in a similar manner to Step 4 of Example 16, 4,7-dichloro-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (38.8 mg, 0.115 mmol) was dissolved in nitromethane (1.6 mL), and the solution was treated with trifluoroacetic acid (0.177 mL, 2.30 mmol) and triethylsilane (55.1 mL, 0.345 mmol), followed by purification by slurry using chloroform/methanol and by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to obtain 4,7-dichloro-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (16.8 mg, yield 72%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-a6f2ceabf1f34466a72d6dc411d700eb
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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