C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][N+:12]=1[O-:19].[CH3:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1.[I-].[K+].[N-]=C=O.C(=O)([O-])[O-]>O1CCCC1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:23]2[CH2:24][CH2:25][CH2:26][CH:21]([CH3:20])[CH2:22]2)=[CH:13][N+:12]=1[O-:19]PS-Diisopropylethylamine (3.54 mmol/g, 0.4 g, 1.40 mmol) was washed with tetrahydrofuran and 2-chloro-5-(chloromethyl)pyridine 1-oxide (100 mg, 0.56 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) was added followed by tetrahydrofuran (1 mL). A solution of 3-methylpiperidine in tetrahydrofuran (1.5 mL) and a catalytic amount of potassium iodide were added, and the mixture was gently stirred (80 r/min) at room temperature for 5 days. PS-Isocyanate (1.10 mmol/g, 1.27 g, 1.40 mmol) was washed with tetrahydrofuran and added to the mixture followed by additional tetrahydrofuran (2 mL). The suspension was gently stirred (80 r/min) at room temperature overnight. N-Ethyl-N,N-diisopropylamine (50 μL, 0.28 mmol) and MP-Carbonate (2.55 mmol/g, 0.66 g, 1.68 mmol) were added, and the containts were mixed and gently stirred for 24 h. The mixture was filtered (20 μm polyethylene filter), and the resins were washed with methylene chloride. Volatiles were removed in vacuo to give 138 mg (99% yield) of the title compound: MS (ES) m/z 241 (M++1).
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