Sodium Hydroxide → HCID 49779777, compound

Participants

Reaction Conditions

Reaction Steps

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (183 mg, 0.917 mmol), tetra n-butyl ammonium bromide (14 mg, 0.045 mmol), and (1-(pyridin-4-yl)cyclopropyl)methyl methanesulfonate (250 mg, 1.10 mmol) were taken into 50% NaOH (6 mL). The reaction mixture was stirred overnight at 100° C. Reaction was monitored by TLC and LCMS. After completion of the reaction, reaction mixture was extracted with EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography to yield 37 mg of product. 1H NMR (CDCl3, Freebase) d (ppm): 8.45 (d, 2H), 7.1-7.0 (m, 3H), 6.9 (d, 2H), 4.28 (s, 2H), 3.63 (s, 2H), 2.7 (t, 2H), 2.5-2.6 (m, 5H), 2.42 (s, 3H), 1.0-0.85 (m, 4H).

Provenance & Evidence