1-(Prop-2-yn-1-yl)pyrrolidine → 7-Chloro-2-(4-phenoxy-benzyl)-5-(3-pyrrolidin-1-yl-prop-1-ynyl)-2,3-dihydro-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-prop-2-ynyl-pyrrolidine (0.024 mL, 0.22 mmol), 5-bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.086 g, 0.20 mmol), PdCl2(PPh3)2 (0.011 g, 0.015 mmol), and CuI (0.0028 g, 0.015 mmol) in diisopropyl amine (4 mL) was stirred at 100° C. for 2 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 7-chloro-2-(4-phenoxy-benzyl)-5-(3-pyrolidin-1-yl-prop-1-ynyl)-2,3-dihydro-isoindol-1-one (0.061 g, 66%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.83 (m, 4H), 2.65 (m, 4H), 3.64 (s, 2H), 4.23 (s, 2H), 4.76 (s, 2H), 6.93-7.38 (m, 10H), 7.43 (s, 1H).

Provenance & Evidence