[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:29])[O:4][N:3]=1.B(F)(F)F.S(C)C.O>C(Cl)Cl.CO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:29])[O:4][N:3]=12-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-methoxyphenyl)-1H-indole-1-carboxamide (8 mg, 0.02 mmol) was dissolved in 8 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.40 ml) was added drop wise and the mixture was stirred at 0-2° C. for 16 h. A few drops MeOH were added followed by water. The layers were separated and the organic layer was concentrated. The crude product was purified by preparative HPLC. 3.4 mg 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide was obtained. ES/MS m/z: 376.1 (pos. M+H), 374.2 (neg. M−H); 1H NMR (acetone-d6, 500 MHz): 7.90 (m, 1H), 7.63 (m, 1H), 7.33 (m, 1H), 7.23 (m, 1H), 7.14 (m, 2H), 6.88 (m, 2H), 3.38 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H) and 1.16 (t, 3H, J=7.3 Hz).
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