Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][C:3]=12.[C:25]([O:29][C:30](=[O:40])[NH:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([F:39])[CH:33]=1)([CH3:28])([CH3:27])[CH3:26].C1(C2C=CC=CC=2C2C(C(C)C)=C(C3CCCCC3)C(C(C)C)=C(P)C=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:25]([O:29][C:30](=[O:40])[NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:10][C:3]=23)=[C:34]([F:39])[CH:33]=1)([CH3:28])([CH3:26])[CH3:27]4-Chloro-2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (312 mg, 0.87 mmol) and (3-fluoro-4-hydroxy-phenyl)-carbamic acid t-butyl ester (336 mg, 1.48 mmol) were dissolved in anhydrous toluene (5 mL) under nitrogen atmosphere. After adding dicyclohexyl-phosphino-2,4,6-triisopropylbiphenyl (41 mg, 0.087 mmol), Pd2 dba3 (40 mg, 0.044 mmol) and potassium carbonate, the mixture was heated at 110° C. The resulting reaction mixture was cooled to room temperature and filtered by passing through a celite pad. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane: ethyl acetate=9:1) to give the target compound as a white solid (404 mg, 0.73 mmol, 84% yield).
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