Potassium Carbonate → 3-bromo-4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one

HRID 1831937ノート

反応式

HRID 1831937 の反応式
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:26]=1[CH2:27]Br>CC(C)=O>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:27][C:26]1[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:25]=1[F:24]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724177HCID 54724177、化合物

生成物 1

HCID 102165503-bromo-4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one (0.20 g, 0.67) and K2CO3 (0.27 g, 1.34 mmol) in acetone (10 mL) was added 2,4-difluorobenzyl bromide (0.16 g, 0.8 mmol), and the reaction mixture was heated at reflux for 1 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with water and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure. 1H NMR (300 MHz, CDCl3) δ 7.65-7.55 (m, 1H), 7.40-7.25 (m, 2H), 7.15-6.80 (m, 5H), 6.14 (d, J=8 Hz, 1H), 5.22 (s, 2H), 5.16 (s, 2H). ES HRMS m/z 424.0159 (M+H C19H14BrF3NO2 requires 424.0155).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic solution was washed with water
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b9fe9d8b9a384aee999b7a4f532f60d7
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

読み込み中…