Potassium Phosphate, Tribasic → 6-(benzylthio)-1-(2-bromo-4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

HRID 1504410

Reaktionsgleichung

Reaktionsgleichung von HRID 1504410
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:43][C:44]1[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[CH:46][C:45]=1I.[NH2:55][C:56]1[CH:61]=[CH:60][C:59]([S:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)=[CH:58][C:57]=1/[CH:70]=[CH:71]/[C:72]([O:74]CC)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:63]([S:62][C:59]1[CH:58]=[C:57]2[C:56](=[CH:61][CH:60]=1)[N:55]([C:45]1[CH:46]=[CH:47][C:48]([C:50]([F:53])([F:52])[F:51])=[CH:49][C:44]=1[Br:43])[C:72](=[O:74])[CH:71]=[CH:70]2)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 117740420(E)-Ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate

Produkt 1

HCID 1177371566-(benzylthio)-1-(2-bromo-4-(trifluoromethyl)phenyl)quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of xantphos (0.277 g, 0.479 mmol), Pd2(dba)3 (0.146 g, 0.160 mmol), 2-bromo-1-iodo-4-(trifluoromethyl)benzene (Oakwood Chemical, 1.232 g, 3.51 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (1.000 g, 3.19 mmol), and potassium phosphate (2.032 g, 9.57 mmol) in 10 mL dioxane was heated to 90° C. for 5 hours. The reaction mixture was diluted with water and extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was used in the next step without purification. m/z (ESI) 536.0 (M+H)+.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was used in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-adde6805a2f240528c0b58d70b40fcf3
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212182B2

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