Cesium fluoride → Ethyl 3-{3'-[(tert-butylsulfonyl)methyl]-4'-chloro-2-(3-methoxypropoxy)biphenyl-4-yl}propanoate

HRID 1690635노트

반응식

HRID 1690635 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[CH:11][C:12]=1OS(C(F)(F)F)(=O)=O.[C:28]([S:32]([CH2:35][C:36]1[CH:37]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:39]=[CH:40][C:41]=1[Cl:42])(=[O:34])=[O:33])([CH3:31])([CH3:30])[CH3:29].[F-].[Cs+]>COCCOC.C(O)C>[C:28]([S:32]([CH2:35][C:36]1[CH:37]=[C:38]([C:12]2[CH:11]=[CH:10][C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:39]=[CH:40][C:41]=1[Cl:42])(=[O:34])=[O:33])([CH3:31])([CH3:29])[CH3:30]

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 669063052-{3-[(Tert-butylsulfonyl)methyl]-4-chlorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86633298Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate

생성물 1

HCID 66906561Ethyl 3-{3'-[(tert-butylsulfonyl)methyl]-4'-chloro-2-(3-methoxypropoxy)biphenyl-4-yl}propanoate수율 39.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate (1.1 g, 2.65 mmol) was dissolved in 1,2-dimethoxyethane (15.7 ml) and ethanol (1.5 ml). 2-{3-[(tert-butylsulfonyl)methyl]-4-chlorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.09 g, 2.92 mmol) was added and argon was bubbled in the solution for 10 minutes. Cesium fluoride (0.89 g, 5.84 mmol) and palladium tetrakistriphenylphosphine (0.153 g, 0.13 mmol) were: added for 2.5 hours. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in ethyl acetate and water. The organic phase was washed with saturated aqueous ammonium chloride and brine, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1) giving 0.53 g (39%) of the desired product.

후처리

  1. customargon was bubbled in the solution for 10 minutes
  2. additionadded for 2.5 hours
  3. customsolvents were evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic phase was washed with saturated aqueous ammonium chloride and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1)

출처 및 근거

ORD 기록
ord-8c6d1f57410e41be9669c1b18d99a366
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153647B2

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