Water → 5-Bromo-4-(cyclopropylmethoxy)-1-(methylsulfonylmethyl)pyridin-2-one

HRID 518543Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:5](=[O:11])[N:6]([CH2:8][S:9][CH3:10])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:25])C=1.[OH2:28]>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:5](=[O:11])[N:6]([CH2:8][S:9]([CH3:10])(=[O:25])=[O:28])[CH:7]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution of the title compound from Step 3 (150 mg, 0.5 mmoL) in DCM (5 mL), was added mCPBA (340 mg, 1.9 mmol). The mixture was stirred at 15° C. for 2.5 hours. Water (30 mL) was added and the resulting mixture was extracted with EtOAc (120 mL×3). The combined organic phases were washed with saturated brine (40 mL×2), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE: EA=5:1 to 2:1) to afford the title compound (120 mg, 72%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.60 (s, 1H), 5.91 (s, 1H), 5.10 (s, 2H), 3.89 (d, J=6.8 Hz, 2H), 2.98 (s, 3H), 0.90-0.86 (m, 1H), 0.75-0.70 (m, 2H), 0.45-0.42 (m, 2H). LCMS: 335.9 (M+1)+; 337

Workup

extractionthe resulting mixture was extracted with EtOAc (120 mL×3)
washThe combined organic phases were washed with saturated brine (40 mL×2)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (PE: EA=5:1 to 2:1)

Sources & evidence

ORD record: ord-e1cd39b322664ca99f7f8470627e0eff
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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