Triphenylphosphine → 3-[2-Ethyl-5-(4-methyl-thiazol-2-yl)phenyl]bicyclo[3.2.1]octane-2,4-dione

HRID 72268

Reaktionsgleichung

Reaktionsgleichung von HRID 72268
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]2[C:14](=[O:15])[CH:13]3[CH2:16][CH:10]([CH2:11][CH2:12]3)[C:9]2=[O:17])[CH:7]=1.[CH3:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(=O)([O-])[O-].[Ag+2].C(#N)C.O>[CH2:18]([C:5]1[CH:4]=[CH:3][C:2]([C:23]2[S:24][CH:25]=[C:21]([CH3:20])[N:22]=2)=[CH:7][C:6]=1[CH:8]1[C:14](=[O:15])[CH:13]2[CH2:16][CH:10]([CH2:11][CH2:12]2)[C:9]1=[O:17])[CH3:19]

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 127484-MethylthiazoleHCID 666795693-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione

Produkt 1

HCID 684874603-[2-Ethyl-5-(4-methyl-thiazol-2-yl)phenyl]bicyclo[3.2.1]octane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (200 mg, 0.62 mmol), 4-methylthiazole (74 mg, 0.75 mmol), silver carbonate (860 mg, 3.1 mmol), triphenylphosphine (16.3 mg, 62.2 umol) and [1,1-bis(diphenylphosphino)ferrocene]palladium(II)chloride (26 mg, 31.1 umol) are added to a scintillation vial and shaken with a degassed solvent mixture of acetonitrile:water 1:1 (1.5 ml) at 65° C. for 22 hours. The mixture is concentrated under reduced pressure, taken up in DMSO (1.5 ml), filtered and purified by preparative reverse-phase HPLC to give 3-[2-ethyl-5-(4-methyl-thiazol-2-yl)phenyl]bicyclo[3.2.1]octane-2,4-dione.

Aufarbeitung

  1. concentrationThe mixture is concentrated under reduced pressure
  2. filtrationfiltered
  3. custompurified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-378924b09e91429c919bfc9e486505e2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828908B2

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