Toluene → HCID 67342335, Verbindung

HRID 2038447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038447
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>CCOC(C)=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.[Pd].CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]([F:34])([F:33])[F:22])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 67344690HCID 67344690, Verbindung

Produkt 1

HCID 67342335HCID 67342335, VerbindungAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzeneKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To title compound of Step D (0.106 g, 0.296 mmol), 2-trifluoromethylphenylboronic acid (0.084 g, 0.444 mmol), K3PO4 (0.189 g, 0.888 mmol), Pd(dba)2 (0.007 g, 0.012 mmol) and QPhos (0.004 g, 0.006 mmol) was added PhCH3 (3 mL) and the reaction was heated to 80° C. for 18 h. The reaction was cooled to rt, diluted with EtOAc, filtered through a small silica plug and concentrated. Silica gel chromatography (0-30% EtOAc in hexanes) gave 0.062 g (49%) of the title compound. MS (ESI): mass calcd. for C22H24F3NO4, 423.17; m/z found, 368.1 [M-56]+, 446.2 [M+Na]+. 1H NMR (CDCl3): 7.73 (d, J=7.8 Hz, 1H), 7.55 (t, J=7.3 Hz, 1H), 7.46 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.93 (s, 2H), 6.56 (s, 1H), 4.92-4.83 (m, 1H), 4.26 (dd, J=10.5, 6.5 Hz, 2H), 4.10 (dd, J=10.5, 4.3 Hz, 2H), 3.93 (s, 3H), 1.43 (s, 9H).

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through a small silica plug
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fbda97f2390e479aa36fa57f6d9dae27
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575364B2

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