Cl[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(C(F)(F)F)=O.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:2]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:6][CH:5]=[CH:4][C:3]=23)=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1To a N2 purged round bottom flask was added 4-chloro-7-azaindole (15.8 g, 104 mmol, 1.0 eq.) followed by 4-benzyloxyphenol (41.5 g, 207 mmol, 2.0 eq), 20 ml of TFA/Et3N (1/1, 107 mmol, 1.0 eq.) and DMAP (13 g, 106 mmol, 1.0 eq.). The reaction was heated to 140° C. for 48 h. The mixture was cooled to RT and diluted with CH2Cl2 (100 mL) Silica gel was added and the mixture was evaporated to dryness onto the silica. The crude mixture was purified by column chromatography (20-100% EtOAc/Hexane) to give 4-(4-benzyloxy-phenoxy)-1H-pyrrolo[2,3-b]pyridine.
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