Triethylamine → 2-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethy}-benzoic acid ethyl ester

HRID 227273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227273
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:6]1.C(N(CC)CC)C.[CH2:27]([O:29][C:30](=[O:41])[C:31]1[CH:36]=[C:35]([CH2:37]Br)[CH:34]=[CH:33][C:32]=1[O:39][CH3:40])[CH3:28]>ClCCl>[CH2:27]([O:29][C:30](=[O:41])[C:31]1[CH:36]=[C:35]([CH2:37][N:17]2[CH2:18][CH2:19][CH:14]([C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH:6]=3)[CH2:15][CH2:16]2)[CH:34]=[CH:33][C:32]=1[O:39][CH3:40])[CH3:28]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 117370201-(2-methoxyethyl)-3-piperidin-4-yl-1H-indoleHCID 688939465-Bromomethyl-2-methoxybenzoic acid ethyl ester

Produkt 1

HCID 689704652-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethy}-benzoic acid ethyl esterAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Over a solution of 6.5 g (0.025 mol) of 1-(2-methoxyethyl)-3-piperidin-4-yl-1H-indole in 90 ml of dichloromethane and 3.9 ml (0.026 mol) of triethylamine, a solution of 7.2 g (0.026 mol) of 5-bromomethyl-2-methoxy-benzoic acid ethyl ester in 15 ml of dichloromethane was added. The crude mixture was stirred at room temperature for 24 hours. After standard work-up and purification by chromatography over silica gel, 9.9 g (70% of yield) of 2-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethy}-benzoic acid ethyl ester were obtained.

Aufarbeitung

  1. customAfter standard work-up and purification by chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ba98b9a34d0b46e9bb9b77d83bdda0fe
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560471B2

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