Trifluoroacetic acid → 4-Bromo-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one

HRID 21339Notes

Reaction equation

HRID 21339 reaction equation
[Br: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[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[Br:1][C:2]1[C:7]2[C:8](=[O:21])[NH:9][CH2:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86628337HCID 86628337, compound

Product 1

HCID 768481334-Bromo-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-oneYield 34%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-bromo-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (239 mg, 0.688 mmol) was dissolved in nitromethane (12 mL), and the solution was treated with trifluoroacetic acid (1.17 mL, 15.1 mmol) and triethylsilane (0.440 mL, 2.75 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 4-bromo-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (49.1 mg, yield 34%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-1c154c18124c483081af4cb314070f73
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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