[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2.CO.CCOCC>C(#N)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2Add dropwise oxalic acid (1.44 g, 1.2 eq.) in acetonitrile to an acetonitrile solution of 4-fluorotryptamine with vigorous stirring. Warm add MeOH to make a solution. Add Et2O to the cloud point and cool the solution in the freezer to give a solid. Collect the solid by filtration and dry in a vacuum oven overnight at 45° C. to give the title compound as a tan solid: 1H NMR (300 MHz, d6-DMSO): 3.07 (m, 4H), 6.73 (m, 1H), 7.04 (m, 1H), 7.22 (m, 2H), 11.30 (bs, 1H); MS (ES+): m/z 179 (M+H)+; (ES−): m/z 177 (M−H)−.
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