Cesium carbonate → 7-Fluoro-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)isoquinolin-3-amine

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Pd2(dba)3(102 mmg, 0.11 mmol) and xantphos (92 mg, 0.16 mmol) were added to a solution of 7-fluoroisoquinolin-3-amine (182 mg, 1.12 mmol) (Preparation C-11), 2-chloro-4-pyrrolidin-1-ylmethyl-pyridine (220 mg, 1.12 mmol) (Preparation B-11) and Cs2CO3 (500 mg, 1.53 mmol) in toluene (50 mL). The suspension was heated under reflux overnight, and THF (50 mL) was added in to dilute the mixture. After filtration, the filtrate was concentrated. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/1) and afforded the title compound (115 mg, 31.8% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 8.94 (s, 1H), 8.42 (s, 1H), 8.27 (d, J=5.4 Hz, 1H), 7.72˜7.77 (m, 2H), 7.33˜7.46 (m, 2H), 7.02 (s, 1H), 6.84 (d, J=5.4 Hz, 1H), 3.59 (s, 2H), 2.55 (m, 4H), 1.81 (m, 4H); MS: m/z 323.1 (M+H+).

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