Tributylvinyltin → HCID 69099575, Verbindung

HRID 2251527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251527
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.[CH:37]([Sn](CCCC)(CCCC)CCCC)=[CH2:38].[Cl-].[Li+].[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[CH3:22][C:16]([O:15][C:14]1[CH:24]=[CH:25][C:11]([CH2:10][CH2:9][N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:5]2[CH:4]=[CH:3][C:2]([CH:37]=[CH2:38])=[CH:7][N:6]=2)=[CH:12][CH:13]=1)([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

10

Edukt 4

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 59643333HCID 59643333, Verbindung

Produkt 1

HCID 69099575HCID 69099575, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 314042,6-Di-tert-butyl-4-methylphenolKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-[4-(2-{(5-bromopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (150 mg; 0.27 mmol) in 2 ml of toluene was treated under nitrogen with tetrakis(triphenylphosphine)palladium (0) (61 mg; 0.053 mmol), vinyltributyltin (252 mg; 0.80 mmol), lithium chloride (34 mg; 0.80 mmol) and 2,6-di-tert-butyl-4-methyl-phenol (3 mg). The mixture was heated at 110C overnight. Upon cooling, the mixture was diluted with 10 ml each of ethyl acetate and water. A saturated solution of KF (10 ml) was added and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (5–50%) afforded ethyl 2-methyl-2-(4-{2-[[4-(trifluoromethyl)benzyl](5-vinylpyridin-2-yl)amino]ethyl}phenoxy)propanoate (71 mg; 52% yield).

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe phases were separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by radial chromatography

Quellen und Nachweise

ORD-Eintrag
ord-166a4e085fd94cf3b86f361809af57f2
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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