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

HRID 1623728노트

반응식

HRID 1623728 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 67106885Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoate

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-088e69db93d34b3186bf98653ead45b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778939B2

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