Water → 5-Bromo-3-(cyclohexylmethoxy)pyridin-2-amine

HRID 64399Notes

Reaction equation

HRID 64399 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]N1C(=O)CCC1=O.O.C(OCC)(=O)C>C(O)(=O)C>[Br:16][C:13]1[CH:14]=[C:9]([O:8][CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:10]([NH2:15])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 138258903-(Cyclohexylmethoxy)pyridin-2-amine

Product 1

HCID 867134085-Bromo-3-(cyclohexylmethoxy)pyridin-2-amineYield 81.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2 g of 3-(cyclohexylmethoxy)pyridin-2-amine in 10 ml of acetic acid was added 1.90 g of N-bromosuccinimide over 30 minutes under ice-cooling, followed by stirring for 30 minutes under ice-cooling. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.25 g of 5-bromo-3-(cyclohexylmethoxy)pyridin-2-amine.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customa layer separation operation
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-71b818eff00b4a15b4f2b33f482133f5
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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