N-bromobutanimide → 5-(6-Amino-5-bromopyridin-3-yl)piperidin-2-one

HRID 595911Notes

Reaction equation

HRID 595911 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[Br:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1180454365-(6-Aminopyridin-3-yl)piperidin-2-one

Product 1

HCID 1180463525-(6-Amino-5-bromopyridin-3-yl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(6-aminopyridin-3-yl)piperidin-2-one (132 mg, 0.690 mmol) in Acetonitrile (8.00 mL) was added NBS (98 mg, 0.552 mmol) at 0° C. The reaction mixture was stirred for 30 min upon warming-up to room temperature. LCMS 0.28 min, MH+270/272; 0.7 min, MH+400.1/402.1 (SEM protected one). After quenched with Na2S2O3 solution, the reaction mixture was extracted with EtOAc, which was washed with NaHCO3 solution and brine. The organic layer was dried over anhydrous Na2SO4, filtered off, concentrated in vacuo. The crude 5-(6-amino-5-bromopyridin-3-yl)piperidin-2-one was used for the next step.

Workup

  1. customLCMS 0.28 min, MH
  2. custom0.7 min, MH
  3. customAfter quenched with Na2S2O3 solution
  4. extractionthe reaction mixture was extracted with EtOAc, which
  5. washwas washed with NaHCO3 solution and brine
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07f3a6fb310940799de8d032032ca477
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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