Dimethyl Sulfoxide → HCID 58423294, compound

HRID 1398014Notes

Reaction equation

HRID 1398014 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:11][N:12]([CH3:18])[C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[C:3]([N:15]2[CH2:16][CH2:17][C@H:13]([N:12]([CH3:18])[CH3:11])[CH2:14]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 220193613-Bromo-2-fluorobenzaldehyde

Product 1

HCID 58423294HCID 58423294, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A 50 mL round bottom flask was charged with a magnetic stir bar, 3-bromo-2-fluorobenzaldehyde (0.555 g, 2.73 mmol), (S)-N,N-dimethylpyrrolidin-3-amine (0.312 g, 2.73 mmol), DMSO (5.47 ml), and potassium carbonate (0.378 g, 2.73 mmol). The mixture was heated to 85° C. overnight with stirring. The reaction was allowed to cool to ambient temperature, was diluted with water, and extracted into methylene chloride. The combined organic extract was dried with MgSO4, filtered, and conc. in vacuo to provide the product which was purified via silica gel chromatography (40 g) using ethyl acetate/MeOH (10:1) as eluent to afford (S)-3-bromo-2-(3-(dimethylamino)pyrrolidin-1-yl)benzaldehyde (0.369 g, 45.4%).

Workup

  1. additionA 50 mL round bottom flask was charged with a magnetic stir bar
  2. temperatureto cool to ambient temperature
  3. extractionextracted into methylene chloride
  4. extractionThe combined organic extract
  5. dry with materialwas dried with MgSO4
  6. filtrationfiltered
  7. customconc. in vacuo to provide the product which
  8. customwas purified via silica gel chromatography (40 g)

Sources & evidence

ORD record
ord-4ea2dd2c8b754f898f31ec81248bb4ad
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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