Cesium carbonate → ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

HRID 84275Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]([CH3:14])([S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[I:15][C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[C:17]=1[CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[I:15][C:16]1[CH:21]=[CH:20][N:19]([CH2:2][CH2:3][C:4]([CH3:14])([S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:18](=[O:22])[C:17]=1[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (2.08 g, 7.25 mmol) and 4-iodo-3-methylpyridin-2(1H)-one (1.42 g, 6.04 mmol) in tetrahydrofuran (60.4 mL) was added cesium carbonate (4.06 g, 12.1) at ambient temperature. The resulting mixture was stirred at 50° C. overnight. The mixture was allowed to cool to ambient temperature and filtered through a celite pad. The pad was washed with ethyl acetate and the filtrate was concentrated to a crude residue. The material was purified via filtration through a silica gel pad, eluting with heptanes/ethyl acetate. The desired fractions were isolated, the solvent removed via rotary evaporation affording ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate as an oil. 1.97 g

Workup

temperatureto cool to ambient temperature
filtrationfiltered through a celite pad
washThe pad was washed with ethyl acetate
concentrationthe filtrate was concentrated to a crude residue
filtrationThe material was purified via filtration through a silica gel pad
washeluting with heptanes/ethyl acetate
customThe desired fractions were isolated
customthe solvent removed via rotary evaporation

Sources & evidence

ORD record: ord-ae3625238b924fd3be119d12e7021e06
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846933B2

Reaction notes

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