Cl.CCCCCC[CH2:8][CH3:9].CC[N:12]([CH:16]([CH3:18])C)[CH:13]([CH3:15])C.Cl[C:20]1[N:24]([CH3:25])[N:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27].[F-].[K+].CS(C)=[O:33]>O>[CH3:25][N:24]1[C:20]([N:12]2[CH2:13][CH:15]3[O:33][CH:18]([CH2:8][CH2:9]3)[CH2:16]2)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]18-Oxa-3-azabyclo[3.2.1]octane hydrochloride (150 mg, 1.0 mmol) and DIPEA (0.26 mL, 1.5 mmol) were stirred in DMSO (4 mL) for 15 min at room temperature. 5-Chloro-1-methyl-4-nitro-1H-pyrazole (150 mg, 0.95 mmol) and potassium fluoride (170 mg, 3 mmol) were then added and the reaction mixture was heated at 70° C. for 18 hr. The mixture was allowed to cool to room temperature and poured into water (4 mL). The aqueous was extracted with EtOAc (3×10 mL) and the combined organic layers were washed with brine (10 mL), separated, dried over MgSO4 and concentrated under reduced pressure to give 3-(1-methyl-4-nitro-1H-pyrazol-5-yl)-8-oxa-3-azabicyclo[3.2.1]octane (220 mg, 92%). 1H NMR (400 MHz CDCl3) δ 8.04 (s, 1H), 4.43 (s, 2H), 3.86 (s, 3H), 3.73-3.70 (m, 2H), 2.61-2.58 (m 2H), 2.09-2.07 (m, 4H).
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