Allyl bromide → HCID 86681223, compound

HRID 1848250Notes

Reaction equation

HRID 1848250 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[CH:16]=[CH2:17]>CN(C=O)C>[CH2:17]([O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178507942HCID 178507942, compound

Product 1

HCID 86681223HCID 86681223, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-aminopyridin-4-ol (500 mg, 4.5 mmol) in DMF (5 mL) at rt was added K2CO3 (940 mg, 6.8 mmol). The resulting mixture was stirred at rt for 20 min before allyl bromide (393 μL, 4.5 mmol) was added. The mixture was then stirred at rt overnight and heated at 60° C. for 2 h. After cooling to rt, the mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by silica gel chromatography eluting with EtOAc in hexanes to give 4-(allyloxy)pyridin-2-amine (110 mg, 16%) as a white solid. LCMS (ESI) m/z 151 (M+H)+.

Workup

  1. additionwas added
  2. temperatureheated at 60° C. for 2 h
  3. temperatureAfter cooling to rt
  4. customthe mixture was partitioned between EtOAc and water
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-8c5cf9e58bcb4beba3a9fba38813cc03
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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