Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CO>C(#N)C.ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([O:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]The mixture of 4-chloro-6-iodo-quinoline (217.5 mg, 1 mmol, prepared by similar procedure to example 1e), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.75 mmol), and 1-tert-butyl-2,2,4,4-pentakis(dimethylamino)-2λ5, 4λ5-catenadi(phosphazene) in tetrahdyrofuran (2M, 0.75 ml, 1.5 mmol) in acetonitrile (3.5 ml) was stirred at 100° C. for 30 min in microwave instrument (Personal Chemistry). After cooling the reaction, the solvent was evaporated, followed by addition of water, some of sodium carbonate saturated solution. The resulting solution was extracted with dimethylene chloride three times. The combined organic layer was dried over the brain, sodium sulfate, then evaporated to give a reddish gel. Flash chromatography (Merck silica gel 60, 230-400 mesh, 0%-3% methanol in dichloromethane for 30 min) afforded 4-(6-iodo-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (262.5 mg, 77%) as A light yellow solid. LC-MS m/e 455 (MH+).
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