N-bromobutanimide → 4-(6-Amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one

HRID 595916Notes

Reaction equation

HRID 595916 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118054586(+/-)-4-(6-Aminopyridin-3-yl)-1-methylpiperidin-2-one

Product 1

HCID 1180545914-(6-Amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (+/−)-4-(6-aminopyridin-3-yl)-1-methylpiperidin-2-one (291 mg, 1.418 mmol) in acetonitrile (14.200 mL) was added NBS (202 mg, 1.134 mmol) at 0° C. The reaction mixture was stirred for 30 min upon warming-up to room temperature. 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 product (+/−)-4-(6-amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one (98%) was used for the next step. LCMS (m/z): 284/286 (MH+), 0.34 min.

Workup

  1. customAfter quenched with Na2S2O3 solution
  2. extractionthe reaction mixture was extracted with EtOAc, which
  3. washwas washed with NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo
  7. custom284/286 (MH+), 0.34 min.

Sources & evidence

ORD record
ord-58b1500f41cb4e9199c4c8dd8876de13
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…