Triethylamine → Vinyl 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carboxylate

HRID 36892

Reaktionsgleichung

Reaktionsgleichung von HRID 36892
Cl[C:2]([O:4][CH:5]=[CH2:6])=[O:3].C(N(CC)CC)C.[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[S:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>ClCCl>[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[S:24][CH:25]1[CH2:30][CH2:29][N:28]([C:2]([O:4][CH:5]=[CH2:6])=[O:3])[CH2:27][CH2:26]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 78808Vinyl chloroformateHCID 199366675-bromo-3-(piperidin-4-ylthio)-1H-indole

Produkt 1

HCID 19936620Vinyl 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Vinyl chloroformate (0.75 ml) is added dropwise to a solution of triethylamine (1.2 ml) and 5-bromo-3-(piperidin-4-ylthio)-1H-indole (2.5 g, prepared in Example 49) in dichloromethane (25 ml) at 0° C. After 2 hours at room temperature, the solution is washed with water. The organic phase is dried over magnesium sulfate and concentrated. Vinyl 4-[(5-bromo-1H-indol-3-yl)thio]piperidine-1-carboxylate (1.8 g) is obtained after chromatography on silica gel (eluent: cyclohexane/AcOEt 70/30).

Aufarbeitung

  1. washthe solution is washed with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1b910d7bef7849f3b7e40343de7732e6
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418242

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