Triethylamine → HCID 58127218, compound

HRID 1963887Notes

Reaction equation

HRID 1963887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[O:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH2:16])[CH2:11][CH2:10]1.C(N(CC)CC)C>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([NH:16][CH2:15][CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 58127218HCID 58127218, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-bromo-6-fluoropyridine (3 g, 17.05 mmol) in DMSO (8 mL) was added (tetrahydro-2H-pyran-4-yl)methanamine (3.10 g, 20.46 mmol) and triethylamine (5.68 mL, 40.9 mmol). The mixture was heated at 110° C. for 18 hr. The mixture was allowed to cool to ambient temperature and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3 solution (1×), water (1×), brine (1×), dried over Na2SO4, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel providing 6-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine as a white solid. Yield: 4.24 g. LCMS (m/z): 270.9/273.0 [M+H]+; Retention time=0.78 min.

Workup

  1. temperatureto cool to ambient temperature
  2. washThe organic layer was washed with saturated aqueous NaHCO3 solution (1×), water (1×), brine (1×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-4412f3fca04a44fd9cff14cbdf5fa642
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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