Potassium Phosphate, Tribasic → [5-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethylpropyl}-phenyl)-pyridin-3-yl]-acetic acid methyl ester

HRID 547068노트

반응식

HRID 547068 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:50]([C:52]([C:70]1[CH:83]=[CH:82][C:73]([O:74][CH2:75][C:76](=[O:81])[C:77]([CH3:80])([CH3:79])[CH3:78])=[C:72]([CH3:84])[CH:71]=1)([C:55]1[CH:60]=[CH:59][C:58](B2OC(C)(C)C(C)(C)O2)=[CH:57][CH:56]=1)[CH2:53][CH3:54])[CH3:51].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:12])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:58]2[CH:57]=[CH:56][C:55]([C:52]([C:70]3[CH:83]=[CH:82][C:73]([O:74][CH2:75][C:76](=[O:81])[C:77]([CH3:80])([CH3:79])[CH3:78])=[C:72]([CH3:84])[CH:71]=3)([CH2:50][CH3:51])[CH2:53][CH3:54])=[CH:60][CH:59]=2)[CH:10]=1

참가 물질

9

반응물 5

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetateHCID 574435241-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one

생성물 1

HCID 57709068[5-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethylpropyl}-phenyl)-pyridin-3-yl]-acetic acid methyl ester수율 73%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 28.6 mg, 0.124 mmol), palladium acetate (1.8 mg, 0.008 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (7.0 mg, 0.017 mmol), potassium phosphate (53 mg, 0.249 mmol) and water (0.2 mL) were added to a solution of 1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (Example 143-(4); 39.7 mg, 0.083 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for two 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=1:1) to give the target compound as a colorless oil (30.4 mg, 73%).

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=1:1)

출처 및 근거

ORD 기록
ord-0d73d991e200479685241809c6f68f12
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

반응 노트

불러오는 중…