Br[CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[N+:9]([C:12]1[N:13](CC#C)[CH:14]=[CH:15][N:16]=1)([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N+:9]([C:12]1[N:13]([CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4])[CH:14]=[CH:15][N:16]=1)([O-:11])=[O:10]
To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H).
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