Methanol → Methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylate

HRID 1403924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403924
O=S(Cl)Cl.[C:5]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=2[C:21]([OH:23])=[O:22])([CH3:8])([CH3:7])[CH3:6].[CH3:24]O>>[C:5]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=2[C:21]([O:23][CH3:24])=[O:22])([CH3:8])([CH3:6])[CH3:7]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 534211852-Tert-butyl-5-nitro-1H-indole-7-carboxylic acid

Produkt 1

HCID 53436897Methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylateAusbeute 70 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

SOCl2 (3.6 g, 30 mol) was added dropwise to a solution of 2-tert-butyl-5-nitro-1H-indole-7-carboxylic acid (4.0 g, 15 mol) and methanol (30 mL) at 0° C. The mixture was stirred at 80° C. for 12 h. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (5% EtOAc in petroleum ether) to afford methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylate (2.95 g, 70%). 1H NMR (CDCl3, 300 MHz) δ 9.99 (brs, 1H), 8.70 (d, J=2.1 Hz, 1H), 8.65 (d, J=2.1 Hz, 1H), 6.50 (d, J=2.4 Hz, 1H), 4.04 (s, 3H), 1.44 (s, 9H).

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was purified by column chromatography on silica gel (5% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-13180c61371e4d4589c5ac370f03c4a0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912199B2

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