Bromine → 5-(Benzyloxy)-3-bromopyridin-2-amine

HRID 2277252Notes

Reaction equation

HRID 2277252 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]Br.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:16])[C:12]([NH2:15])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 223152765-(Benzyloxy)pyridin-2-amine

Product 1

HCID 582090735-(Benzyloxy)-3-bromopyridin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(benzyloxy)pyridin-2-amine (10.2 g) in acetic acid (50 mL) was added bromine (2.61 mL) at 0° C., and the mixture was stirred for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (8.50 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aa492df8b50740169374dbc757993210
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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