[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH2:18]O)=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.S(Cl)([Cl:27])=O>C(Cl)Cl.C(O)C>[ClH:1].[Cl:27][CH2:18][C:14]1[N:15]=[CH:16][C:17]2[N:5]([CH2:4][C:3]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:2]=3[Cl:1])[C:6]3[C:11]([C:12]=2[CH:13]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3A solution of [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methanol (7.14 g, 20 mmol) in anhydrous CH2Cl2 (100 mL) was cooled to 0° C. under nitrogen atmosphere, and thionyl chloride (2.5 g, 20.8 mmol) was added dropwise with stirring. The solution was allowed to warm to room temperature and stirred for another 15 hours. The reaction mixture was diluted with anhydrous ethanol (50 mL) and concentrated on a rotary evaporator to give a pale-yellow solid. The crude material was crystallized by addition of anhydrous ether, affording 6.92 grams (84%) of 3-chloromethyl-9-(2,5-dichlorobenzyl)-9H-β-carboline hydrochloride. This salt was converted to the free base by addition of aqueous Na2CO3 and then extracting the resulting mixture with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated in vacuo to give 0.30 g (100%) of the free base as a pale yellow solid. 1H NMR (CDCl3) δ8.72 (s, 1H), 8.20 (d, J=7.9, 2.3 Hz, 1H), 8.18 (s, 1H), 7.60 (t,J=7 Hz, 1H), 7.38 (m, 3H), 7.20 (dd, J=8.3, 2.3 Hz, 1H), 6.55 (s, 1H), 5.65 (s, 2H), 4.92 (s, 2H); MS monoisotopic mass (calculated) 374.0, MH+(observed) 375.2, (MH+−HCl) 339.1.
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