N,N,N',N'-Tetramethylazodicarboxamide → 2-{[6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine

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Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][C:4]=1[OH:21].N(C(N(C)C)=O)=NC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:54][CH2:55][NH:56]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][C:4]=1[O:21][CH2:54][CH2:55][NH2:56]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To 6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 15, 2.0 g, 6.6 mmol), 1,1′-azobis(N,N-dimethylformamide) (2.3 g, 13 mmol), triphenylphosphine (3.5 g, 13 mmol), tert-butyl N-(2-hydroxy-ethyl)carbamate (2.1 g, 13 mmol) and DCM (40 mL) were added. The mixture was heated at 150° C. for 20 minutes in a microwave heater. The reaction mixture was allowed to cool to room temperature and TFA (30 mL) was added. The reaction mixture was allowed to stir at room temperature for 30 minutes. The solvent was removed under reduced pressure and the crude material was purified by flash chromatography on silica gel using 5% MeOH in DCM as the eluent to afford the title compound (2.53 g) MS m/z 347 [M+H]+.

Aufarbeitung

temperatureto cool to room temperature
customThe solvent was removed under reduced pressure
customthe crude material was purified by flash chromatography on silica gel using 5% MeOH in DCM as the eluent

Quellen und Nachweise

ORD-Eintrag: ord-158f3b77cef44415a896850bbc800ec2
Quelldatensatz: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07960374B2

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