[NH2:1][C:2]1[C:3]([C:7](=[N:16][OH:17])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=2)=[N:4][O:5][N:6]=1.[CH2:18]([OH:21])[C:19]#[CH:20].C(NCC)C>CN(C)C=O.C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:1][C:2]1[C:3]([C:7](=[N:16][OH:17])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:20]#[C:19][CH2:18][OH:21])[CH:10]=2)=[N:4][O:5][N:6]=1A solution of 4-amino-N′-hydroxy-N-(3-iodophenyl)-1,2,5-oxadiazole-3-carboximidamide (19 mg, 55 μmol), 2-propyn-1-ol (3.6 μL, 62 μmol), bis(triphenylphosphine)palladium(II) chloride (1 mg, 2 μmol), and copper (I) iodide (0.4 mg, 2 μmol) in N,N-dimethylformamide (0.5 mL) was treated with N,N-diethylamine (74 μL, 0.72 mmol) and heated in the microwave at 120° C. for 15 min. The reaction mixture was diluted with 1:1 acetonitrile/water (1.5 mL), filtered, and purified by preparative LCMS to give the desired product (4 mg, 28%). LCMS for C12H12N5O3 (M+H)+: m/z=274.0.
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