1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopentanecarbonitrile → 1-(4-(5-Amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)phenyl)cyclopentanecarbonitrile

Participants

Reaction Steps

General method A was applied to 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopentanecarbonitrile (149 mg, 0.5 mmol) and 6-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (180 mg, 0.5 mmol) to give 1-(4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)phenyl)cyclopentanecarbonitrile as a yellow solid (89 mg, 0.22 mmol, 44% yield) after purification by preparatory reverse phase HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (s, 1H), 8.02 (d, J=8.3 Hz, 3H), 7.96 (d, J=8.0 Hz, 1H), 7.72-7.78 (m, 1H), 7.70 (s, 1H), 7.57 (m, J=8.5 Hz, 3H), 3.38-3.45 (m, 2H), 2.99 (t, J=6.4 Hz, 2H), 2.37-2.46 (m, 2H), 2.03-2.16 (m, 2H), 1.84-1.94 (m, 4H); MS (EI) m/z=410.5 [M+1]+.

Provenance & Evidence