Dimethyl Sulfoxide → HCID 86642345, compound

HRID 339686Notes

Reaction equation

HRID 339686 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][OH:13])[CH:8]=[CH:7]2.CS(C)=O.S([O-])([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 22622880Pyridine sulfate (2:1)HCID 67233948HCID 67233948, compound

Product 1

HCID 86642345HCID 86642345, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(8-bromo-6-fluoroquinolin-2-yl)methanol (2 g, 7.8 mmol), DMSO (8.9 mL, 125.0 mmol), and TEA (4.9 mL, 35 mmol) were weighed into a flask and dissolved in a 10 mL of DCM, followed by cooling to 0° C. Pyridinium sulfate (4.351 g, 27.3 mmol) was added and the reaction stirred 0° C. for 1 hour. The reaction was poured onto 50 mL water and extracted with ethyl acetate. The combined organics were then dried over MgSO4, then concentrated in vacuo affording a yellow/white semi-solid, which was further purified by triturating with 20% ethyl acetate/Hexanes, affording the desired product as a tan solid (1.35 g, 68% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics were then dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customaffording a yellow/white semi-solid, which
  5. customwas further purified
  6. customby triturating with 20% ethyl acetate/Hexanes

Sources & evidence

ORD record
ord-9372cf98bbcd489b8e89f39ac8bc40f7
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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