[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N:23]1([CH2:22][CH2:21][CH2:20][O:16][C:13]2[CH:14]=[CH:15][C:10]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[N:2]3)=[CH:11][CH:12]=2)[CH2:27][CH2:26][CH2:25][CH2:24]14-Indazol-1-yl-phenol (0.07 mmol) was dissolved in N,N′-dimethylformamide (0.5 mL), and sodium hydride (3 mg, 60% dispersion in mineral oil, 0.085 mmol), 1-(3-chloropropyl)pyrrolidine (10 mg, 0.07 mmol) and a catalytic amount of sodium iodide were added. The reaction was heated at 70° C. for 2.5 hours. Saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic extracts were dried over MgSO4, concentrated, and purified by semi-prep LC-MS to give 3.5 mg of the desired product. LC-MS (C20H23N3O calculated 321) m/z 322 (M+H).
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