8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → HCID 59454914, compound

Participants

Reaction Steps

8-Chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (500 mg, 2.27 mmol) was dissolved in DMF (10 mL). Copper (I) iodide (86 mg, 0.452 mmol), L-proline (0.075 g, 0.652 mmol) and potassium phosphate (0.963 g, 4.54 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 4-(1-Bromo-3-methylbut-1-en-2-yl)pyridine (0.65 g, 2.87 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 100° C. (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh). The product was further purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.50 (d, 2H), 7.60 (d, 2H), 7.40 (s, 1H), 7.10 (d, 2H), 7.05 (s, 1H), 4.70 (m, 1H), 4.30 (m, 1H), 3.80 (m, 1H), 3.50 (m, 1H), 3.10 (m, 6H), 1.30 (d, 6H).

Provenance & Evidence