Potassium Phosphate, Tribasic → (4'-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)acetic acid methyl ester

HRID 546934노트

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HRID 546934 반응식
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:38]([C:40]([C:59]1[CH:64]=[CH:63][C:62](/[CH:65]=[CH:66]/[C:67]([C:73]([F:76])([F:75])[F:74])([OH:72])[C:68]([F:71])([F:70])[F:69])=[C:61]([CH3:77])[CH:60]=1)([C:43]1[CH:48]=[CH:47][C:46](B2OC(C)(C)C(C)(C)O2)=[C:45]([CH3:58])[CH:44]=1)[CH2:41][CH3:42])[CH3:39].[CH3:78][O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:87]=[CH:86][CH:85]=[C:84](Br)[CH:83]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:78][O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:83]=[C:84]([C:46]2[CH:47]=[CH:48][C:43]([C:40]([CH2:41][CH3:42])([C:59]3[CH:64]=[CH:63][C:62](/[CH:65]=[CH:66]/[C:67]([OH:72])([C:73]([F:75])([F:76])[F:74])[C:68]([F:71])([F:70])[F:69])=[C:61]([CH3:77])[CH:60]=3)[CH2:38][CH3:39])=[CH:44][C:45]=2[CH3:58])[CH:85]=[CH:86][CH:87]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 57708964(E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol

생성물 1

HCID 57709177(4'-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)acetic acid methyl ester수율 31%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Palladium acetate (3.6 mg, 0.016 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (13.1 mg, 0.032 mmol), potassium phosphate (51 mg, 0.24 mmol) and water (0.04 mL) were added to a solution of (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 40 mg, 0.070 mmol) and (3-bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 28 mg, 0.122 mmol) in toluene (0.4 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 30 minutes. Then, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane. Thereafter, the solution was filtered through amino silica gel, and the filtrate was 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 (12.8 mg, 31%).

후처리

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationThereafter, the solution was filtered through amino silica gel
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-ae6a49e8a49a48de8e638898fd4c556d
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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