[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)#[CH:2].[N-:10]=[N+:11]=[N-:12].[Na+].IC.[Na].O=[C:18]1O[C@H]([C@H](CO)O)C(O)=C1O>O.ClCCl.[Cu]I>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]2[N:10]=[N:11][N:12]([CH3:18])[CH:2]=2)=[CH:4][CH:5]=1
The reaction mixture was splitted in 24 tubes of 1.00 g (8.32 mmol) each. A mixture of 1-ethynyl-4-fluorobenzene (24.0 g, 200 mmol), sodium azide (14.41 g, 222 mmol), iodomethane (14.93 mL, 240 mmol), copper(I) iodide (8.03 g, 42 mmol) and L-(+)-ascorbic acid sodium salt (7.84 g, 40 mmol) in water (240 mL) was heated at 75° C. for 10 h. The mixture was then diluted with dichloromethane (25 mL) and filtered off. The aqueous layer of the filtrate was extracted with dichloromethane and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 5% methanol in dichloromethane) afforded the title compound (20.3 g, 57%) as a white solid after recrystallisation from ethyl acetate-heptane. MS: m/e=178.1 [M+H]+.
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