Sodium Hydroxide → methyl 1-(3-tert-butoxycarbonylaminopropyl)-1H-indole-2-carboxylate

HRID 564970

Reaktionsgleichung

Reaktionsgleichung von HRID 564970
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[OH-].[Na+].I[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>CN(C)C=O>[C:23]([O:22][C:21]([NH:20][CH2:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11])=[O:27])([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 70992Methyl 1H-indole-2-carboxylateHCID 11231463tert-butyl N-(3-iodopropyl)carbamate

Produkt 1

HCID 10830411methyl 1-(3-tert-butoxycarbonylaminopropyl)-1H-indole-2-carboxylateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The reaction was carried out in a manner similar to Reference Example 5 except for using 5.00 g (28.5 mmol) of methyl 2-indolecarboxylate, 1.26 g (31.4 mmol) of 60% sodium hydroxide, 12.3 g (43.2 mmol) of tert-butyl N-(3-iodopropyl)carbamate (prepared from 3-iodopropyl-amine and di-tert-butyl dicarbonate) and 60 ml of dimethylformamide. Thus, 2.54 g (27%) of methyl 1-(3-tert-butoxycarbonylaminopropyl)-2-indolecarboxylate was obtained.

Quellen und Nachweise

ORD-Eintrag
ord-0897eb3eed3143c18f23b3bf0bddb633
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169107A

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