Dimethyl Sulfoxide → HCID 58564193, compound

HRID 1425965Notes

Reaction equation

HRID 1425965 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[O:9]1[CH2:13][CH2:12][C@@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:11]2[CH2:12][CH2:13][O:9][CH2:10]2)[C:4](=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridineHCID 11149197Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-

Product 1

HCID 58564193HCID 58564193, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-1H-pyridin-2-one (0.50 g), (R)-toluene-4-sulfonic acid tetrahydrofuran-3-yl ester (0.40 g), potassium carbonate (0.80 g), and dimethylsulfoxide (5 mL) was stirred at 80° C. overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by HPLC on reversed phase (acetonitrile/water) to afford the title compound [besides, 4-bromo-2-[(S)-tetrahydro-furan-3-yloxy]-pyridine was isolated in 0.36 g (56% of theory)]. Yield: 0.11 g (16% of theory); LC (method 3): tR=2.18 min; Mass spectrum (ESI+): m/z=244/246 (Br) [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC on reversed phase (acetonitrile/water)

Sources & evidence

ORD record
ord-d2fe45627f3b450392bdee69a86ba338
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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