Dimethylformamide → {3-[7-(3-Diethylamino-prop-1-ynyl)-5,5-dioxo-5H-5lambda6-dibenzothiophen-3-yl]-prop-2-ynyl}-diethylamine

HRID 902976

Reaktionsgleichung

Reaktionsgleichung von HRID 902976
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[S:7](=[O:16])(=[O:15])[C:6]=2[CH:17]=1.[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][C:22]#[CH:23])[CH3:19].[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:27].[CH3:33]N(C=O)C>CCOC(C)=O.Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][C:22]#[C:23][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:33]#[C:27][CH2:26][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:13][C:8]=3[S:7](=[O:16])(=[O:15])[C:6]=2[CH:17]=1)[CH3:19]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 20010DietylaminopropinHCID 40718983,7-Dibromo-dibenzothiophene 5,5-dioxide

Produkt 1

HCID 67163580{3-[7-(3-Diethylamino-prop-1-ynyl)-5,5-dioxo-5H-5lambda6-dibenzothiophen-3-yl]-prop-2-ynyl}-diethylamineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418903HCID 178418903, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3,7-dibromodibenzothiophene 5,5-dioxide (0.33 g, 0.88 mmol; see J. Med. Chem. 1978, 21, 1084), 3-diethylamino-1-propyne (0.5 mL, 3.4 mmol; Lancaster), triethylamine (0.6 mL, 4.2 mmol; Acros), dichlorobis(triphenylphosphino)palladium(II) (Cl2Pd(PPh3)2; 25 mg, 0.035 mmol; Aldrich), and copper(I) iodide (38 mg, 0.20 mmol; Aldrich) in DMF (10 mL) was heated to 65° C. for 60 h. The reaction mixture was diluted with EtOAc, washed with water and brine, and dried over Na2SO4. The residue was purified by chromatography (16 g silica gel, 2-7% gradient MeOH in CH2Cl2to afford the title compound (0.31 g, 0.71 mmol, 82% yield): MS (DCl/NH3) m/z 435 (M+H)+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe residue was purified by chromatography (16 g silica gel, 2-7% gradient MeOH in CH2Cl2to

Quellen und Nachweise

ORD-Eintrag
ord-b40e7644f83343a7a88643ebda83fd87
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365193B2

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