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

HRID 1623728ノート

反応式

HRID 1623728 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+].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CC(C)=O>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][C:2]2[CH:11]=[CH:10][C:9]([C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 67107453Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

生成物 1

HCID 67106885Methyl 2-{[(4-fluorophenyl)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 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 4-fluorobenzyl bromide (0.16 ml, 1.32 mmol). The mixture was heated at 50° C. for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (15 ml) and water (5 ml). The organic layer was dried and the solvent removed in vacuo and the residue purified by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane) to give the title compound as a yellow gum. 96 mg.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (15 ml) and water (5 ml)
  3. customThe organic layer was dried
  4. customthe solvent removed in vacuo
  5. customthe residue purified by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane)

出典と根拠

ORDレコード
ord-088e69db93d34b3186bf98653ead45b0
出典データセット
uspto-grants-2014_07
特許番号
US08778939B2

反応ノート

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