Triethylamine → HCID 57828221, Verbindung

HRID 1644231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644231
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=[CH:5]2.[CH2:20]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][C:22]#[CH:23].C(N(CC)CC)C>C1COCC1.Cl[Pd](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>[Si:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:23]#[C:22][CH2:21][CH2:20][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:11]=[CH:10]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneHCID 21185506HCID 21185506, Verbindung

Produkt 1

HCID 57828221HCID 57828221, VerbindungAusbeute 38,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (6-bromonaphthalen-2-yloxy)(tert-butyl)dimethylsilane (81, 16.1 g, 47.7 mmol), benzyl but-3-ynylcarbamate (82, 9.0 g, 47.7 mmol), and triethylamine (95 mL) in anhydrous THF (100 mL) was cooled to −78° C. and degassed with argon. The mixture was warmed to room temperature and dichlorobis(triphenylphosphine)palladium(II) (3.3 g, 4.8 mmol) and CuI (1.8 g, 9.6 mmol) were added rapidly in one portion under argon. The mixture was heated at 50° C. for 12 h. The reaction mixture was filtered through a plug of diatomaceous earth and the filtrate was concentrated. The residue was purified by column chromatography (silical gel, 10:1 hexanes/EtOAc) to afford carbamate 83 (8.5 g, 38%) as a thick brown oil: 1H NMR (300 MHz, CDCl3) δ 7.83 (s, 1H), 7.65 (d, J=9.0 Hz, 1H), 7.60 (d, J=8.7 Hz, 1H), 7.39-7.29 (m, 6H), 7.13 (d, J=2.1 Hz, 1H), 7.07 (dd, J=8.7, 2.4 Hz, 1H), 5.17 (br s, 1H), 5.13 (s, 2H), 3.46 (q, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.01 (s, 9H), 0.25 (s, 6H).

Aufarbeitung

  1. customdegassed with argon
  2. temperatureThe mixture was heated at 50° C. for 12 h
  3. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silical gel, 10:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-cd7a5eb9f5db4f46b81f3bea36c74064
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124607B2

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