Reaction Steps
A solution of 1-methyl-2-{[methyl(prop-2-yn-1-yl)amino]methyl}-1H-indol-5-ol (8) (Cruces, M. A.; Elorriaga, C.; Fernández-Álvarez, E. Eur. J. Med. Chem. 1991, 26, 33-41) (0.215 g, 0.942 mmol), 1,2-dibromoethane (1.77 g, 9.42 mmol), and potassium carbonate (0.65 g, 4.71 mmol) in 2-butanone (8 mL) was heated at 85° C. for 6 h. The mixture was evaporated under vacuum and the residue was extracted with dichloromethane (10 mL) and water (10 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by column chromatography, eluting with a 4% methanol mixture in dichloromethane to give compound 9 (117.3 mg, 37%). Rf=0.76 (CH2Cl2/AcOEt, 10/1); pf 75-77° C.; RMN of 1H (300 MHz, CDCl3) δ 2.31 (t, J=2.4 Hz, 1H, ≡CH), 2.36 (s, 3H, N—CH3), 3.32 (d, J=2.4 Hz, 2H, N—CH2—C≡), 3.66 (t, J=6.4 Hz, 2H, —CH2—Br), 3.69 (s, 2H, N—CH2), 3.75 (s, 3H, N—CH3), 4.33 (t, J=6.4 Hz, 2H, —CH2—O—), 6.36 (s, 1H, CH3), 6.9 (dd, J=8.8, 2.5 Hz, 1H, CH6), 7.07 (d, J=2.4 Hz, 1H, CH4), 7.2 (d, J=8.8 Hz, 1H, CH7); RMN of 13C (75 MHz, CDCl3) δ 29.6 (CH2—Br), 29.9 (N—CH3), 41.5 (N—CH3), 44.7 (—CH2—C≡), 51.7 (CH2—N), 69.1 (CH2—O), 73.5 (≡CH), 78.3 (—C≡), 102.15 (CH3ind), 104.42 (CH4ind), 109.7 (CH7ind), 112.2 (CH6ind), 127.4 (C3aind), 133.8 (C7aind), 137.3 (C2ind), 152.2 (C5ind); EM (IE) m/z (%): 131 (48), 160 (66) [M-((Br(CH2)2)—NCH3CH2C≡CH)]+, 267 (100) [M-NCH3CH2C≡CH)]+, 334 (25)[M]+
