Potassium Carbonate → HCID 59135243, compound

HRID 1028553Notes

Reaction equation

HRID 1028553 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C@@H:12]1[O:16][C:15](=[O:17])[NH:14][C@H:13]1[CH3:18].[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26](B(O)O)[CH:27]=1)([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[C@@H:12]2[O:16][C:15](=[O:17])[NH:14][C@H:13]2[CH3:18])[CH:27]=1)([CH3:21])[CH3:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 59287354HCID 59287354, compound

Product 1

HCID 59135243HCID 59135243, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 0.036 g of trans-5-[2-iodo-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one, 0.024 g of (5-isopropyl-2-methoxyphenyl)boronic acid, and 0.04 g of potassium carbonate in 2 mL of acetone and 0.5 mL of water was added ca. 2 mg of palladium acetate. The mixture was heated to reflux and stirred at this temperature for 1.5 h. Acetone was removed by rotary evaporation and the residue was diluted with 10 mL of EtOAc and 10 mL of water. The aqueous phase was extracted with 10 mL of EtOAc. The combined organics were washed with 10 mL of brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 25S column, eluting with 1 CV of 10% EtOAc in hexanes, followed by a linear gradient of EtOAc in hexanes from 10 to 100% over 10 CV to provide the title compound. Mass spectrum (ESI) 394.2 (M+1). 1H NMR signals are doubled because of atropoisomerism. 1H NMR (500 MHz, CDCl3): δ 7.80, 7.78 (s, 1H), 7.64, 7.63 (d, J˜8 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.27, 7.26 (d, J˜8 Hz 1H), 7.00, 6.95 (d, J=2.5 Hz, 1H), 6.93, 6.92 (d, J˜8 Hz, 1H), 5.87, 5.81 (s, 1H), 5.16, 5.10 (d, J˜5 Hz, 1H), 3.70-3.78 (m, 3.5H), 3.49 (m, 0.5H), 2.89 (m, 1H), 1.24 (m, 6H), 0.90, 0.70 (d, J=6.5 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customAcetone was removed by rotary evaporation
  4. additionthe residue was diluted with 10 mL of EtOAc and 10 mL of water
  5. extractionThe aqueous phase was extracted with 10 mL of EtOAc
  6. washThe combined organics were washed with 10 mL of brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on a Biotage Horizon, 25S column
  10. washeluting with 1 CV of 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-d319af2215c64181b3e4216b42a996d3
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

Loading…