C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[C:16]([C:18]([NH2:20])=[O:19])[O:15][N:14]=2)=[CH:9][CH:8]=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[F-].[K+].[Br:49][C:50]1[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=1[CH2:52]Br>CN(C=O)C.O>[Br:49][C:50]1[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=1[CH2:52][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:17]=[C:16]([C:18]([NH2:20])=[O:19])[O:15][N:14]=2)=[CH:11][CH:12]=13-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 13; 40 mg, 0.126 mmol) was dissolved in DMF (1.5 mL). K2CO3 (19 mg, 0.14 mmol), 18-crown-6 (5 mg, 0.02 mmol), KF (8 mg, 0.14 mmol), and 2-bromobenzyl bromide (20 mg, 0.10 mmol) were added. The reaction mixture was stirred at room temperature for 10 min and then at 40° C. for 12 h. H2O (2.5 mL) was added and the mixture was extracted with EtOAc. The organic layer was evaporated and purified by chromatography (35% EtOAc/hexanes) to give 3-[4-(2-bromo-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (7.5 mg, 16%) as a white powder. LRMS (ESI+): m/z [M+H]+ 376.1. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.35 (s, 1H), 7.98 (s, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.64-7.72 (m, 1H), 7.59 (d, J=7.7 Hz, 1H), 7.53 (s, 1H), 7.39-7.48 (m, 1H), 7.26-7.36 (m, 1H), 7.16 (d, J=8.8 Hz, 2H), 5.19 (s, 2H).
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