Potassium Carbonate → 3-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-one

HRID 1790152Notes

Reaction equation

HRID 1790152 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[O:19]=[C:20]1[N:24]([CH2:25][CH2:26]OS(C)(=O)=O)[CH2:23][CH2:22][O:21]1>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:26][CH2:25][N:24]2[CH2:23][CH2:22][O:21][C:20]2=[O:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 446271152-(2-Oxooxazolidin-3-yl)ethyl methanesulfonate

Product 1

HCID 220365783-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-oneYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-(2-hydroxy-ethyl)-oxazolidin-2-one (1.00 g, 7.63 mmol) and Hunigs base (2.92 mL, 16.8 mmol) in dichloromethane (19 mL) at 0° C. was added mesyl chloride (0.650 mL, 8.40 mmol) slowly via syringe. The mixture was stir cold for three hours, diluted with 10 mL of water and 25 mL of dichloromethane. The layers were separated and the organic layer was washed with aqueous NaHCO3 (3×30 mL) followed by water (1×15 mL). The organic layer was then dried (Na2SO4), filtered, and concentrate under reduced pressure to provide 650 mg of methanesulfonic acid 2-(2-oxo-oxazolidin-3-yl)-ethyl ester as a light brown oil. In a separate flask 6-nitroindazole (318 mg, 1.95 mmol) was treated with potassium carbonate (538 mg 3.9 mmol) in DMF (10 mL) for 30 minutes, afer which methanesulfonic acid 2-(2-oxo-oxazolidin-3-yl)-ethyl ester (490 mg 2.34 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours, cooled to room temperature, filtered through a plug of silica gel and rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (210 mg, 39% yield). 1H NMR (300 MHz, DMSO-d6) ppm 3.49 (m, 2H), 3.62 (t, J=5.76, 2H), 4.13 (m, 2H), 4.76 (t, J=5.76, 2H), 7.97–8.03 (m, 2H), 8.33 (m, 1H), 8.83 (m, 1H); MS (DCI/NH3) m/z 277 [M+H]+.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a plug of silica gel
  4. washrinsed with triethylamine/ethyl acetate (1/4)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-b43d88ecf0c54ba2b4e9d777cbce85ac
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

Loading…