Potassium tert-butoxide → HCID 59603103, Verbindung

HRID 2068707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068707
[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([CH3:27])=[CH:15][C:14]=1Br)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>O1CCOCC1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:20]([O:19][C:17]1[C:16]([CH3:27])=[CH:15][C:14]2[S:11][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:12][C:13]=2[CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 59603075HCID 59603075, Verbindung

Produkt 1

HCID 59603103HCID 59603103, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-benzoyl-3-(5-benzyloxy-2-bromo-4-methyl-phenyl)-thiourea II (1.0 g, 2.20 mmol) in 1,4-dioxane (30 mL) was added sequentially Pd2(dba)3 (0.12 g, 0.12 mmol), dppf (0.07 g, 0.12 mmol) and KOtBu (0.75 g, 3.30 mmol) at room temperature under N2 atmosphere. The resulting reaction mixture was heated at 80° C. for 6 h. After completion of reaction (TLC monitoring), the reaction mixture was diluted with EtOAc and filtered through celite bed-bed. The filtrate was concentrated and purified over silica gel (100-200 M, 20% EtOAc-Hexane) to obtain the desired product (0.50 g, 61%). 1H NMR (400 MHz, DMSO-d6): δ 2.31 (s, 3H), 5.23 (s, 2H), 7.33 (m, 1H), 7.39 (m, 3H), 7.52 (m, 2H), 7.54 (m, 2H), 7.64 (m, 1H), 7.76 (s, 1H), 8.13 (d, J=7.60 Hz, 2H) and 12.77 (br s, 1H). MS: 375.19 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter completion of reaction (TLC monitoring)
  3. filtrationfiltered through celite bed-bed
  4. concentrationThe filtrate was concentrated
  5. custompurified over silica gel (100-200 M, 20% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4eb605fc06f84ef7885e9178de426cd7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299065B2

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