N-bromobutanimide → 3-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 595933Notes

Reaction equation

HRID 595933 reaction equation
[CH3:1][C:2]1([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)Cl.C(OCC)(=O)C>[Br:22][C:10]1[C:11]([NH2:14])=[N:12][CH:13]=[C:8]([C:2]2([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]2)[CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1180456035-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

Product 1

HCID 1180457983-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amineYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (50 mg, 0.26 mmol) in DCM (5 mL) was added NBS (50.9 mg, 0.28 mmol) in two portions. The reaction mixture was stirred at ambient temperature for 40 min. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered off, and concentrated to give 3-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (70 mg, 0.26 mmol, 99% yield) as yellow color residue. LCMS (m/z): 271/273 (MH+), 0.41 min.

Workup

  1. washwashed with water, aqueous sodium bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6db9f113010a4b6ab8578b077a581f68
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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