m-Chloroperbenzoic acid → 3H-Pyrrolo[2,3-b]pyridin-3-one, 1,2-dihydro-1-(methylsulfonyl)-

HRID 489733Notes

Reaction equation

[CH3:1][S:2]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7](C=O)=[CH:6]1)(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[CH3:1][S:2]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7](=[O:24])[CH2:6]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Methanesulfonyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.84 g, 12.7 mmol) from step 2 was dissolved in dichloromethane (150 ml) and cooled to 0° C. Meta-chloroperbenzoic acid (3.4 g, 15 mmol) was added in several portions. The reaction mixture was stirred under a nitrogen atmosphere overnight, while slowly warming to room temperature. The reaction mixture was filtered through a plug of basic alumina and concentrated under reduced pressure to a yellow solid. The crude product was chromatographed over silica gel eluting with 50% ethyl acetate in hexane to yield 1-methanesulfonyl-1,2-dihydro-pyrrolo[2,3-b]pyridin-3-one (700 mg, 26%). 1H NMR (DMSO-d6) δ: 3.59 (3H, s), 4.60 (2H, s), 7.45 (1H, dd, J=4.9 Hz, 7.7 Hz), 8.31 (1H, dd, J=1.8 Hz, 7.7 Hz), 8.84 (1H, dd, J=1.8 Hz, 4.9 Hz).

Workup

temperaturewhile slowly warming to room temperature
filtrationThe reaction mixture was filtered through a plug of basic alumina
concentrationconcentrated under reduced pressure to a yellow solid
customThe crude product was chromatographed over silica gel eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-3c5196f5af794f3db45dcc6e89b41a12
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979696B2

Reaction notes

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