N,N,N',N'-Tetramethylazodicarboxamide → [Rac]-2-{6-[2-methyl-5-(4-trifluoromethoxy-phenyl)-2h-pyrazol-3-ylmethoxy]-indol-1-yl}-propionic acid ethyl ester

HRID 915486

Reaktionsgleichung

Reaktionsgleichung von HRID 915486
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[CH:9]=[CH:8]1)[CH3:6])[CH3:2].[CH3:18][N:19]1[C:23]([CH2:24]O)=[CH:22][C:21]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)=[N:20]1.CN(C)C(N=NC(N(C)C)=O)=O.C(P(CCCC)CCCC)CCC>>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:24][C:23]3[N:19]([CH3:18])[N:20]=[C:21]([C:26]4[CH:27]=[CH:28][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[CH:30][CH:31]=4)[CH:22]=3)[CH:14]=2)[CH:9]=[CH:8]1)[CH3:6])[CH3:2]

Komponenten

5

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 44818672{1-methyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}methanolHCID 68826438[Rac]-2-(6-hydroxy-indol-1-yl)-propionic acid ethyl ester

Produkt 1

HCID 69282790[Rac]-2-{6-[2-methyl-5-(4-trifluoromethoxy-phenyl)-2h-pyrazol-3-ylmethoxy]-indol-1-yl}-propionic acid ethyl ester

Versuchsvorschrift

In analogy to the procedure described for example 3 c], [rac]-2-(6-hydroxy-indol-1-yl)-propionic acid ethyl ester (J. E. D. Barton, D. Cartwright, C. J. Mathews, Brit. UK Pat. Appl. (1992), GB 2253848 A1) was reacted with [2-methyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanol (example 11 d]) in the presence of N,N,N′,N′-tetramethyl azodicarboxamide and tributylphosphine to give [rac]-2-{6-[2-methyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-propionic acid ethyl ester as colorless oil.

Quellen und Nachweise

ORD-Eintrag
ord-789e6102f0f342ca8e4f040e1f0f0da1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265149B2

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