Imidazole → 2-(4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-yl)-6-fluoro-5-nitro-1H-indole

HRID 468515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468515
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][OH:14])[NH:8]2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>C(Cl)Cl>[Si:24]([O:14][CH2:13][CH2:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([N+:17]([O-:19])=[O:18])=[C:2]([F:1])[CH:10]=2)([CH3:16])[CH3:15])([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591293673-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol

Produkt 1

HCID 591294122-(4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-yl)-6-fluoro-5-nitro-1H-indoleAusbeute 52.558.400 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol (6.6 g, 25 mmol) in CH2Cl2 (80 mL) was added TBSCl (3.7 g, 25 nmol) and imidazole (4.2 g, 62 nmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The precipitate was filtered off and washed with the methanol. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1) to give the desired product as a brown solid (5.0 g, 53%). 1H NMR (300 MHz, CDCl3) δ 9.80 (brs, 1H), 8.30 (d, J=7.2 Hz, 1H), 7.05 (d, J=11.7 Hz, 1H), 6.33 (t, J=1.2 Hz, 1H), 3.7 (t, J=6.0 Hz, 2H), 1.91 (t, J=6.0 Hz, 2H), 1.42 (s 6H), 0.94 (s, 9H), 0.12 (s, 6H). MS (ESI) m/z (M+H+): 381.1.

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. washwashed with the methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c20e7c076e440179896474f834d2db4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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