Sodium Carbonate → [6-Chloro-5-(4-chloro-phenyl)-pyridin-3-yl]-((R)-4-isobutyl-2,2-dimethyl-oxazolidin-3-yl)-methanone

HRID 1159227Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:9]([N:11]2[C@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][O:13][C:12]2([CH3:21])[CH3:20])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([C:9]([N:11]2[C@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][O:13][C:12]2([CH3:21])[CH3:20])=[O:10])=[CH:3][C:2]=1[C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(5-Bromo-6-chloro-pyridin-3-yl)-((R)-4-isobutyl-2,2-dimethyl-oxazolidin-3-yl)-methanone (2.0 g, 5.5 mmol) was dissolved in toluene (10 mL). To this solution was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloro-methane complex (226 mg), 4-chlorophenyl-boronic acid (1.34 g, 8.3 mmol), and 2 N sodium carbonate solution (8.3 mL). The whole mixture was heated with stirring at 90° C. for 18 h, cooled to room temperature (RT) and eluted with ethyl acetate over 10 g ChemElut (Varian). The solvent was evaporated and the residue was purified by column chromatography on silica (cyclohexane/ethyl acetate gradient) to yield 0.81 g of the title compound as off-white solid.

Workup

temperatureThe whole mixture was heated
temperaturecooled to room temperature (RT)
washeluted with ethyl acetate over 10 g ChemElut (Varian)
customThe solvent was evaporated
customthe residue was purified by column chromatography on silica (cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-735fb1c1d17a49788a1cf28e36f34842
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812028B2

Reaction notes

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