[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9])#[CH:2].I[CH3:11].[N-:12]=[N+:13]=[N-:14].[Na+]>C(#N)C.O.[Cu]I>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[N:12]=[N:13][N:14]([CH3:11])[CH:2]=1Solution A was composed of 1-ethynyl-2-fluorobenzene (4.2 g, 35 mmol) and iodomethane (5.96 g, 42 mmol) in acetonitrile (94 mL) and Solution B was composed of sodium azide (2.73 g, 42 mmol) and copper(I) iodide (1.33 g, 6.99 mmol) in water (100 mL). The reaction was ran in Uniqsis FlowSyn apparatus at 150° C. at 100 psi with flow rate of 1.0 mL/min and residence time of 1.5 min for each solution A and B. The reaction flow eluent was collected in an aqueous ammonium hydroxide solution (25%) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 10 to 60% ethyl acetate in heptane) afforded the title compound (1.5 g, 24%) as a light yellow solid. MS: m/e=178.3 [M+H]+.
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