1,4-Dibromobenzene → HCID 57420154、化合物

HRID 1619211ノート

反応式

HRID 1619211 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2([OH:26])[CH2:22][CH2:21][N:20]([C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:14]=3)[CH2:25][CH2:24]2)=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 78041,4-DibromobenzeneHCID 14788561-Pyrimidin-2-yl-piperidin-4-oneHCID 178418339Butyllithium

生成物 1

HCID 57420154HCID 57420154、化合物収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1,4-dibromobenzene (213.3 mg, 0.904 mmol) in THF (4 ml), was added n-BuLi (2.5 M in hexanes, 0.362 ml, 0.904 mmol) at −78° C. After being stirred for 30 minutes at the same temperature, a solution of 1-pyrimidin-2-yl-piperidin-4-one (80 mg, 0.452 mmol) in THF (3 ml) was added. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with addition of water (10 ml) and EtOAc (50 ml). The organic layer was washed with brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 4-(4-Bromo-phenyl)-1-pyrimidin-2-yl-piperidin-4-ol as a colorless oil (140 mg, 93%): 1H NMR (CDCl3, 400 MHz) δ 8.33 (d, J=6.4 Hz, 2H), 7.47 (d, J=12.0 Hz, 2H), 7.41 (d, J=12.0 Hz, 2H), 6.49 (t, J=6.4 Hz, 1H), 4.72 (m, 2H), 3.40 (m, 2H), 2.05 (m, 2H), 1.78 (m, 2H); MS calc'd for C15H17BrN3O [M+H]+: 335; Found: 335.

後処理

  1. stirringstirred for 1 hour
  2. customThe reaction was quenched with addition of water (10 ml) and EtOAc (50 ml)
  3. washThe organic layer was washed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto furnish the crude product
  8. customThis material was purified by column chromatography (40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ef881fcb6d9f492c877325aeac9beb88
出典データセット
uspto-grants-2014_07
特許番号
US08772291B2

反応ノート

読み込み中…