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

HRID 595916ノート

反応式

HRID 595916 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-58b1500f41cb4e9199c4c8dd8876de13
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

読み込み中…