Trifluoroacetic acid → 5-(4-Chloro-phenyl)-6-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridin-3-ylamine
Reaktionsgleichung
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([NH:28]C(=O)OC(C)(C)C)[CH:18]=[N:19][C:20]=2[O:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[C:17]([NH2:28])[CH:18]=[N:19][C:20]=2[O:21][C@@H:22]([CH3:27])[C:23]([F:24])([F:25])[F:26])=[CH:13][CH:14]=1Komponenten
3
Versuchsvorschrift
Trifluoroacetic acid (2.74 g, 1.85 ml, 24.0 mmol) was added to (S)-tert-butyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-ylcarbamate (0.350 g, 840 μmol). The resulting yellow solution was stirred at RT for 1 h. The solvent was evaporated. The residue was partitioned between ethyl acetate and 1M Na2CO3 solution, the organic phase was dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 5 to 50% EtOAc in heptane) to give 0.22 g (82%) of the title compound as light brown oil; MS (EI) 317.1 (M+H)+.