Dimethyl Sulfoxide → HCID 71255048, compound

HRID 540321Notes

Reaction equation

HRID 540321 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1.F[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 97462-FluoropyridineHCID 11430Potassium CarbonateHCID 71255050HCID 71255050, compound

Product 1

HCID 71255048HCID 71255048, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 4-chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-6-ol (200 mg, 0.617 mmol), 2-fluoro-pyridine (180 mg, 1.85 mmol), potassium carbonate (73 mg, 0.53 mmol) and dry dimethylsulfoxide was heated with stirring in a sealed tube for 40 minutes at 130° C. under microwave irradiation. The resulting mixture was cooled to room temperature, then diluted with water (10 mL) and extracted with ethyl acetate (10 mL×2). The combined organic layer was washed with brine (10 mL×3), and then dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:5) to give 110 mg of product as a yellow solid (yield was 45%).

Workup

  1. temperaturewas heated
  2. temperatureThe resulting mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (10 mL×2)
  4. washThe combined organic layer was washed with brine (10 mL×3)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:5)

Sources & evidence

ORD record
ord-18be1cde97c14269b7a2e6397264ce3e
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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