Potassium Phosphate, Tribasic → HCID 67540669, compound

Participants

Reaction Steps

A round bottom flask charged with 6-bromo isoquinoline (prepared from 4-bromobenzaldehyde according to the literature: Neiko Nerenz, et al. (1998) J. Chem. Soc. Perkin Trans. 2, 437-447, 0.200 g, 0.961 mmol), 1-Boc piperazine (0.215 g, 1.15 mmol), K3PO4 (0.286 g, 1.35 mmol), (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine (0.028 g, 0.072 mmol) and Pd2dba3 (0.022 g, 0.024 mmol) in dry DME (2 mL) was purged under N2 and heated at reflux for 5 hours. After cooling, the mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (1:1 hexanes/EtOAc,) to give 4-Isoquinolin-6-yl-piperazine-1-carboxylic acid tert-butyl ester (0.210 g, 70%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 9.04 (s, 1H), 8.39 (dd, J=6.8 Hz, J=2.8 Hz, 1H), 7.83 (dd, J=9.2 Hz, J=2.8 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.32 (dd, J=9.2 Hz, J=2.4 Hz, 1H), 6.98 (s, 1H), 3.64 (m, 4H), 3.35 (m, 4H), 1.50 (s, 9H). LCMS (APCI+) m/z 314 [M+H]+; Rt=2.14 minutes.

Provenance & Evidence