Potassium Carbonate → (3S)-1-(5-bromo-2-pyridinyl)-N,N-dimethyl-3-pyrrolidinamine

HRID 423391Notes

Reaction equation

HRID 423391 reaction equation
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[Br:9][C:10]1[CH:11]=[CH:12][C:13](F)=[N:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27831685-Bromo-2-fluoropyridineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidine

Product 1

HCID 60052291(3S)-1-(5-bromo-2-pyridinyl)-N,N-dimethyl-3-pyrrolidinamineYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heat a mixture of dimethyl-pyrrolidin-3-(S)-yl-amine (3.0 g, 26.3 mmoL), 5-bromo-2-fluoro-pyridine (4.62 g, 26.3 mmol), potassium carbonate (7.98 g, 57.8 mmol) in acetonitrile (91 mL) at 80° C. overnight. Allow the mixture to cool to RT, filter with CH2Cl2, and concentrate. Purify the crude material by flash chromatograph, eluting with 5% MeOH (2N NH3)/CH2Cl2 to give 3.55 g (50%) of the title compound. LC-MS/ES m/z (81Br) 272.3 [M+H]+.

Workup

  1. temperatureHeat
  2. filtrationfilter with CH2Cl2
  3. concentrationconcentrate
  4. customPurify the crude material by flash chromatograph
  5. washeluting with 5% MeOH (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-dc03d793da3a44c4b6cefbe3a89c0143
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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