Triethylamine → HCID 58284609, compound

HRID 1623319Notes

Reaction equation

HRID 1623319 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[CH3:9][C:10]1([CH2:16][NH2:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(N(CC)CC)C>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([NH:17][CH2:16][C:10]2([CH3:9])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 54165201(4-Methyloxan-4-yl)methanamine

Product 1

HCID 58284609HCID 58284609, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-bromo-6-fluoropyridine (619 mg, 3.52 mmol) in DMSO (3 mL) was added (4-methyltetrahydro-2H-pyran-4-yl)methanamine (500 mg, 3.87 mmol) and triethylamine (498 mg, 4.93 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 [SiO2, 24 g, EtOAc/heptane=0/100 2 min, 0/100 to 40/60 2-25 min] providing 6-bromo-N-((4-methyltetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine as a white solid. Yield: 750 mg. LCMS (m/z): 285.0/287.0 [M+H]+; Retention time=0.88 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 [SiO2, 24 g, EtOAc/heptane=0/100 2 min, 0/100 to 40/60 2-25 min]

Sources & evidence

ORD record
ord-0675195c1bb44299b0c5d259ef50b1e9
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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