C(O[C:6]([N:8]([CH2:28][C:29]1[CH:34]=CC=CN=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3CCC2)=[CH:12][CH:11]=1)=O)(C)(C)C.BrCC(O[C:40]([CH3:43])([CH3:42])[CH3:41])=O.[C:44](=[O:47])([O-])[O-:45].[K+].[K+].[CH3:50][C:51]#[N:52]>>[N:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:27]=1[CH2:18][NH:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]([CH2:6][C:44]([OH:45])=[O:47])[CH:28]2[C:42]3[N:52]=[CH:51][CH:50]=[CH:41][C:40]=3[CH2:43][CH2:34][CH2:29]2)=[CH:15][CH:14]=1To a solution of N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (230 mg, 0.50 mmol) and t-butyl bromoacetate (0.15 mL, 1.02 mmol) in CH3CN (8 mL) was added powdered potassium carbonate (220 mg, 1.60 mmol) and the mixture was stirred for 16 hours. The crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2 to 95:5) to give the desired product (160 mg, 56%) as a yellow oil.
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