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

HRID 1623729노트

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HRID 1623729 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+].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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-805aab774ace4f6bb78021d601140838
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778939B2

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