[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22]Br>CN(C=O)C.C(OCC)C.O>[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[N:9]1To a mixture of 6-nitroindazole (10.0 g, 61 mmol) and K2CO3 (9.31 g, 67.5 mmol) in DMF (60 mL) at room temperature was added 2-bromoacetaldehyde dimethylacetal (7.98 mL, 67.5 mmol), after which the mixture was heated to 50 C for 18 hours. The mixture was cooled to room temperature, diluted with diethyl ether (60 mL) and H2O (50 mL) and extracted with diethyl ether (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to an orange oil. The residue was purified by MPLC (SiO2, 9:1 Hexane:ethyl acetate to 4:1 Hexane:ethyl acetate) to provide 1-(2,2-dimethoxyethyl)-6-nitro-1H-indazole as an orange oil. 1H NMR (300 MHz, DMSO-D6) δ ppm 3.27 (s, 6 H), 4.71 (d, J=4.75 Hz, 2 H), 4.79 (m, 1 H), 7.97 (m, 2 H), 8.34 (s, 1 H), and 8.76 (s, 1 H); MS (ESI) 252 (M+H)+.
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