Cesium carbonate → HCID 24801837, Verbindung

HRID 883168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883168
[CH2:1]([CH:8]1[CH2:12][NH:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27](Br)=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([N:11]2[CH2:12][CH:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C:10]2=[O:13])=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187848954-Benzylpyrrolidin-2-oneHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Produkt 1

HCID 24801837HCID 24801837, VerbindungAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-benzylpyrrolidin-2-one (0.068 g, 0.39 mmol), N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (0.10 g, 0.32 mmol), cesium carbonate (0.16 g, 0.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.006 g, 0.060 mmol) and xantphos (0.008 g, 0.013 mmol) in anhydrous toluene (3 mL) was subjected to microwave irradiation at 120° C. for 15 min. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexanes (1/1)) to afford the title compound as a white solid (0.017 g, 13%): mp 143-144° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.38-7.11 (m, 10H), 5.91 (br s, 1H), 4.56 (d, J=5.5 Hz, 2H), 4.25-4.13 (m, 1H), 3.85-3.72 (m, 1H), 2.95-2.68 (m, 4H), 2.61 (s, 3H), 2.52-2.39 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 173.0, 162.3, 155.3, 152.6, 138.2, 137.9, 128.8, 128.7, 127.9, 127.6, 126.8, 118.6, 52.6, 44.0, 40.1, 37.7, 33.4, 17.2; MS (ES+) m/z 406.3 (M+1).

Aufarbeitung

  1. customirradiation at 120° C. for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography (ethyl acetate/hexanes (1/1))

Quellen und Nachweise

ORD-Eintrag
ord-ecfa5bab102a40788284b7a89009ec70
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236835B2

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