Cesium carbonate → Methyl 2-([(2,4-difluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoate

HRID 1623729ノート

反応式

HRID 1623729 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[F:35]>CC(C)=O>[F:35][C:29]1[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=1[CH2:27][O:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 67107453Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

生成物 1

HCID 67107388Methyl 2-([(2,4-difluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate (may be prepared as described in Description 108, 270 mg, 1.02 mmol) in acetone (3 ml) was added cesium carbonate (663 mg, 2.04 mmol) and 1-(bromomethyl)-2,4-difluorobenzene (0.17 ml, 1.32 mmol). The mixture was heated at 50° C. for 2 hours, cooled and the solvent removed in vacuo. The residue was partitioned between water (5 ml) and ethyl acetate (10 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a residue. Purification by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane) yielded the title compound as a yellow gum. 100 mg.

後処理

  1. temperaturecooled
  2. customthe solvent removed in vacuo
  3. customThe residue was partitioned between water (5 ml) and ethyl acetate (10 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a residue
  7. customPurification by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane)

出典と根拠

ORDレコード
ord-805aab774ace4f6bb78021d601140838
出典データセット
uspto-grants-2014_07
特許番号
US08778939B2

反応ノート

読み込み中…