[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[OH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]2.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]3)=[CH:6][CH:7]=12-chloro-5-(chloromethyl)pyridine (0.995 g, 6.14 mmol) was added slowly to a well-stirred mixture of 6-hydroxyquinolin-2(1H)-one (0.9 g, 5.58 mmol), K2CO3 (1.158 g, 8.38 mmol) and potassium iodide (0.927 g, 5.58 mmol) in DMF (18 mL) at 40° C. The reaction mixture was stirred at 40° C. for 18 h and poured into ice/water. The suspension was filtered and the filter cake taken up in methanol/DCM and purified by flash chromatography on silica gel using 1-5% (10% ammonium hydroxide in methanol)/DCM. The desired fractions were concentrated to give 6-((6-chloropyridin-3-yl)methoxy)quinolin-2(1H)-one as a beige solid (1.0 g, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.69 (1H, s), 8.55 (1H, d, J=2.01 Hz), 7.98 (1H, dd, J=8.03, 2.51 Hz), 7.85 (1H, d, J=9.54 Hz), 7.58 (1H, d, J=8.03 Hz), 7.18-7.32 (2H, m), 6.51 (1H, d, J=9.54 Hz), 5.19 (2H, s). LCMS: R.T.=3.07; [M+H]+=287.01.
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