8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → 1-(8-Chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(4-fluorophenyl)hexan-2-ol

Participants

Reaction Steps

To a solution of 8-chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (1.3 g, 5 mmol) in dimethylformamide (10 mL) was added sodium hydride (709 mg, 17.7 mmol) in portions followed by addition of 2-butyl-2-(4-fluorophenyl)oxirane (3.4 g, 17.7 mmol), and the reaction mixture was stirred for 18 h at RT. After completion, reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by silica gel (100-200 mesh) column chromatography using 1% MeOH-DCM as eluent. The pure compound was converted into oxalate salt by treatment with oxalic acid in ethanol. 1H NMR (CDCl3, Oxalate salt) d (ppm): 7.30 (m, 3H), 7.10 (d, 1H), 6.95 (m, 3H), 4.20 (m, 1H), 4.0 (m, 1H), 3.62 (m, 2H), 2.70 (m, 3H), 2.50 (s, 3H), 2.20 (m, 1H), 2.0 (m, 1H), 1.80 (m, 1H), 1.22 (m, 3H), 1.0 (m, 1H), 0.80 (t, 3H).

Provenance & Evidence