Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([O:13][CH3:14])=[CH:6]2.CO[C:17]1[CH:18]=N[C:20]2[C:25]([CH:26]=1)=[CH:24][C:23](CO)=[CH:22][CH:21]=2.CS(OS(C)(=O)=O)(=O)=O.C([N:40](CC)CC)C.[Cl-].[Li+].C[N:48]([CH:50]=[O:51])C>>[CH3:14][O:13][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([CH2:2][N:48]1[C:50](=[O:51])[CH:18]=[CH:17][C:26]([C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:40]1)=[CH:12][CH:11]=26-(chloromethyl)-3-methoxyquinoline. To a solution of (3-methoxyquinolin-6-yl)methanol (0.17 g, 0.9 mmol) in DMF (10 mL) was added methanesulfonic anhydride (0.4 g, 2 mmol) followed by triethylamine (0.4 ml, 3 mmol). After stirred for 1 h, lithium chloride (0.08 g, 2 mmol) was added. The reaction was continued to stir at rt under N2 for 20 h. The reaction mixture was quenched with water. The resulting mixture was partitioned between EtOAc/sat. NaHCO3 The organic layer was washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, hex:acetone=90%:10%, Flow=30 mL/min). A peak at 30 min was collected. The solvent was removed in vacuo to afford the desired product as white solid (100 mg). MS (ESI pos. ion) m/z (M+1): 208.4. Calc'd exact mass for C11H10ClNO: 207.66. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.96 (s, 3 H) 4.76 (s, 2 H) 7.37 (d, J=2.78 Hz, 1 H) 7.58 (dd, J=8.62, 1.90 Hz, 1 H) 7.75 (s, 1 H) 8.05 (d, J=8.62 Hz, 1 H) 8.69 (d, J=2.92 Hz, 1 H).
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