[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].Br[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1.O>CC#N>[CH3:1][N:2]([CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1To a solution of N-methyltetrahydro-2H-pyran-4-amine (172.5 mg, 1.5 mmol) in CH3CN (5 mL) was added K2CO3 (207 mg, 1.5 mmol) and 2-bromo-5-nitropyridine (203 mg, 1 mmol). The reaction was stirred at 80° C. for 16 hours. TLC and LC-Ms showed the reaction had completed and the reaction was poured into water, extracted with EA, washed with water and brine, dried and concentrated to give a yellow solid. MS (m/z): 238 (M+H)+
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