Trifluoroacetic acid → 4-Chloro-6-methyl-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

HRID 21345Notes

Reaction equation

HRID 21345 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[CH:5]=[C:4]([CH3:22])[N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[NH:9][CH2:10][C:6]=2[CH:5]=[C:4]([CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 866283414-Chloro-1-hydroxy-6-methyl-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

Product 1

HCID 768481344-Chloro-6-methyl-1,2-dihydropyrrolo[3,4-c]pyridine-3-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-chloro-1-hydroxy-6-methyl-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (70.0 mg, 0.220 mmol) was dissolved in nitromethane (3.5 mL), and the solution was treated with trifluoroacetic acid (0.509 mL, 6.60 mmol) and triethylsilane (0.141 mL, 0.880 mmol), followed by purification by slurry using isopropylether/hexane to obtain 4-chloro-6-methyl-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (25.5 mg, yield 63%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-c6d8e56438df48b69797ef94b9c3998f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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