Br[C:2]1[C:3]2[O:10][CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[Cu](C#N)[C:12]#[N:13].CN(C)C=O>C(OCC)C.[Cu](I)I>[O:10]1[C:3]2[C:2]([C:12]#[N:13])=[CH:7][N:6]=[CH:5][C:4]=2[CH:8]=[CH:9]1Combine 7-bromofuro[3,2-c]pyridine (4.673 g, 23.5 mmol), copper cyanide (4.21 g, 47.1 mmol), copper iodide (8.96 g, 47.1 mmol), and anhydrous dimethylformamide (100 mL) and at 130° C. for 30 hours. Cool to room temperature, dilute with diethyl ether and wash with 15% aqueous ammonium hydroxide. Extract combined aqueous layers with diethyl ether, wash combined organic layers with 15% aqueous ammonium hydroxide, and brine, dry over magnesium sulfate, and concentrate. Purification using flash chromatography, eluting with hexane: ethyl acetate gives the tide compound as a white solid.
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