2-(2-Aminoethyl)-1-methylpyrrolidine → N-[2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-alpha]pyridin-7-yl]-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (50 mg, 0.154 mmol) in 1 mL of isopropanol was added excess of 2-(1-methylpyrrolidin-2-yl)ethanamine (1 mL). The mixture was heated to reflux at 85° C. overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give N-[2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridin-7-yl]-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]amine as peach solid in 17% yield (28.3% yield based on recovered starting material). 1H NMR (CDCl3): δ 8.58 (dd, 2H, J=1.4, 4.6 Hz), 7.59–7.62 (m, 2H), 7.25–7.32 (m, 3H), 7.04–7.14 (m, 3H), 6.83 (t, 1H, J=5.3 Hz), 5.98 (d, 1H, J=7.4 Hz), 3.40–3.55 (m, 2H), 3.13–3.19 (m, 1H), 2.43 (s, 3H), 2.36–2.43 (m, 1H), 2.20–2.29 (m, 1H), 1.66–2.20 (m, 6H); MS (ES+ve): 418 (10, M+3), 417 (20, M+2), 416 (60, M+1), 112 (100).

Provenance & Evidence