Pyrrolidine → HCID 59455129, 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, pyrrolidine (0.033 mL, 0.343 mmol) was added to the reaction mixture and the contents heated to 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 25 mg of desired compound as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.78 (d, 2H), 8.18 (d, 2H), 7.68 (s, 1H), 7.50 (s, 1H), 7.39 (d, 1H), 7.24 (d, 1H), 4.78 (m, 1H), 4.45 (m, 1H), 3.90 (m, 1H), 3.74-3.60 (m, 5H), 3.24 (m, 2H), 3.18 (s, 3H), 2.24 (m, 4H), 2.10 (s, 3H).

Provenance & Evidence