N-bromobutanimide → Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

HRID 1875038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875038
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)=[O:15])([CH3:12])[CH3:11]>ClCCl>[Br:1][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:14]([O:13][C:10]([CH3:9])([CH3:11])[CH3:12])=[O:15])[CH:18]=2)[NH:22][C:21]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

Produkt 1

HCID 68484480Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylateAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (0.095 g, 0.536 mmol) was added to a solution of ethyl 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.163 g, 0.536 mmol) in dichloromethane (5 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.186 g, 48%) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.97 (br. s., 1H), 7.70 (s, 1H), 7.28-7.39 (m, 2H), 6.54 (br. s., 1H), 4.33-4.54 (m, 2H), 1.54 (s, 9H), 1.39-1.48 (m, 3H). ES MS: m/z 381, 383.

Aufarbeitung

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7e37500eefd7420fb141a1286809050b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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