Potassium Phosphate, Tribasic → (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-4-methoxy-biphenyl-3-yl)-acetic Acid Methyl Ester

HRID 547146

반응식

HRID 547146 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[O:12][CH3:13].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:52]([C:54]([OH:86])([CH2:84][CH3:85])/[CH:55]=[CH:56]/[C:57]1[CH:62]=[CH:61][C:60]([C:63]([CH2:81][CH3:82])([C:66]2[CH:71]=[CH:70][C:69](B3OC(C)(C)C(C)(C)O3)=[CH:68][CH:67]=2)[CH2:64][CH3:65])=[CH:59][C:58]=1[CH3:83])[CH3:53].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([C:69]2[CH:68]=[CH:67][C:66]([C:63]([CH2:81][CH3:82])([C:60]3[CH:61]=[CH:62][C:57](/[CH:56]=[CH:55]/[C:54]([CH2:84][CH3:85])([OH:86])[CH2:52][CH3:53])=[C:58]([CH3:83])[CH:59]=3)[CH2:64][CH3:65])=[CH:71][CH:70]=2)[CH:8]=[CH:7][C:6]=1[O:12][CH3:13]

참가 물질

9

반응물 5

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 21999895Methyl 2-(5-bromo-2-methoxyphenyl)acetateHCID 57708914(E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol

생성물 1

HCID 57709162(4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-4-methoxy-biphenyl-3-yl)-acetic Acid Methyl Ester수율 64%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

(5-Bromo-2-methoxy-phenyl)-acetic acid methyl ester (Example 180-(1); 40.5 mg, 0.156 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.6 mg, 0.021 mmol), potassium phosphate (66 mg, 0.312 mmol) and water (0.2 mL) were added to a solution of (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 49.7 mg, 0.104 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (35.2 mg, 64%).

후처리

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-69bcdffcb5694f588a8ae29ca99b1308
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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