2-Methoxyethylamine → HCID 59455092, compound

Participants

Reaction Conditions

Reaction Steps

8-Chloro-2-methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.100 g, 0.245 mmol), sodium tertbutoxide (0.283 g, 2.948 mmol), palladium acetate (0.010 g, 0.049 mmol) and 2-di-tertbutylphosphino-2′-4′-6′-triisopropylbiphenyl (0.031 g, 0.0735 mmol) were charged in a reaction bottle which was evacuated and back filled with nitrogen for 5 min. Dry toluene (2 mL) was added under nitrogen atmosphere. Finally, 2-methoxy-ethylamine (0.029 mL, 0.343 mmol) was added and the contents heated at 100° C. overnight. The reaction mixture was filtered and precipitate washed with EtOAc (2×25 mL). The filtrate was concentrated under vacuum and purified by reverse phase chromatography to yield 15 mg of free base. 1H NMR (CDCl3, free base) δ (ppm): 8.60 (d, 2H), 7.40 (d, 2H), 7.10 (s, 1H), 6.96 (d, 1H), 6.62 (d, 2H), 3.80 (m, 2H), 3.64 (t, 2H), 3.40 (s, 3H0, 3.30 (t, 2H), 2.95 (m, 2H), 2.82 (m, 2H), 2.62 (s, 3H), 2.0 (s, 3H).

Provenance & Evidence