m-Chloroperbenzoic acid → 2-Benzyl-3-(2,3-dihydro-benzofuran-5-yl)-2,4-dihydro-pyrrolo[3,4-b]quinolin-9-one

HRID 392040Notes

Reaction equation

HRID 392040 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:14]4[NH:15][C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22](=[O:23])[C:13]=4[CH2:12][N:11]3[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:9][C:4]=2O[CH2:2]1.[CH:31]1C=C(Cl)C=C(C(OO)=O)C=1.CO.C(Cl)Cl>C(Cl)Cl.CN(C=O)C>[CH2:24]([N:11]1[CH:12]=[C:13]2[C:14]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]2=[O:23])=[C:10]1[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:31][C:4]=2[CH:9]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 129930153-Benzo[1,3]dioxol-5-yl-2-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-oneHCID 21226129Dichloromethane methanol

Product 1

HCID 103183492-Benzyl-3-(2,3-dihydro-benzofuran-5-yl)-2,4-dihydro-pyrrolo[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Benzo[1,3]dioxol-5-yl-2-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one, prepared as in WO 01/87882, Example 3, page 45, (39.6 mg, 0.1 mmol) in a mixture of CH2Cl2 (4 mL) and DMF (1 mL) was stirred with a solution of mCPBA (26 mg, 0.15 mmol) in CH2Cl2 (2 mL) at room temperature for 72 h. The product was isolated by preparative TLC (2.5% MeOH/CH2Cl2, Rf=0.72) to yield the title compound as a yellow solid.

Sources & evidence

ORD record
ord-e3eedfc013494c22b7fc78f7144ec105
Source dataset
uspto-grants-2004_10
Patent number
US06800625B2

Reaction notes

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