Potassium Carbonate → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynylamino]-indol-1-yl}-acetic acid ethyl ester

HRID 751208

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].[F:17][C:18]([F:37])([F:36])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][CH2:30][CH2:29][CH2:28][C:27]#[C:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:17])([F:36])[F:37])=[CH:21][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A suspension of (6-amino-indol-1-yl)-acetic acid ethyl ester (50 mg, 0.23 mmol, WO 2003041714 A1), methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester (148 mg, 0.46 mmol) and potassium carbonate (63 mg, 0.46 mmol) in DMF (1 ml) was stirred for 3 h at ambient temperature and for 14 h at 70° C. The reaction mixture was poured onto ethyl acetate/ice water 1/1, the layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, heptane/AcOEt) to give 16 mg (0.03 mmol, 15%) of the title compound as yellow oil.

Aufarbeitung

customthe layers were separated
extractionthe aqueous layer was extracted two times with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried over sodium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography (silica gel, heptane/AcOEt)

Quellen und Nachweise

ORD-Eintrag: ord-cae5d914e0fb4d66935730977703649c
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07405236B2

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