Tetrabutylammonium Fluoride → 3-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium flouride (1M in THF, 5 ml, 5 mmol) was added to 3-[2-(trimethylsilyl)ethoxycarbonylamino]-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 4; 80 mg, 0.2 mmol) and the mixture was heated to 50° C. for 1 hour. The mixture was concentrated in vacuo and the residue was dissolved in DCM and washed with water. The organic phase was separated, dried and evaporated in vacuo. The crude product was purified by flash eluting over a gradient of 0-2.5% MeOH in DCM. The product was obtained as a light brown solid (34 mg) after evaporation of the appropriate fractions. NMR (300 MHz, CDCl3) 8.40 (s, 1H), 8.16 (d, 1H), 7.48 (m, 2H), 7.18 (t, 1H), 4.91 (m, 1H), 3.13 (q, 2H), 1.69 (d, 6H), 1.40 (t, 3H); m/z 255.

Provenance & Evidence