Stannanecarbonitrile, tributyl- → HCID 59631525, compound

Participants

Reaction Steps

A solution of (3-chloro-5-morpholinophenyl)(7-fluoro-3-methyl-2-(pyridin-2-yl)-quinolin-4-yl)methanol (0.050 g, 0.108 mmol), tributyltin cyanide (0.034 g, 0.108 mmol), XPhos precatalyst (CAS 1028206-56-5; 0.014 g, 0.022 mmol), and NMP (1.0 mL) was heated in a microwave at 150° C. for 2 h. Upon completion, the reaction mixture was partitioned between EtOAc and water, and the organic phase was dried over magnesium sulfate and concd. This afforded a crude material that was purified by column chromatography (silica; 0-100% EtOAc in hexanes) to yield 3-((7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)(hydroxy)methyl)-5-morpholinobenzonitrile as an amorphous beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (1H, d), 8.31 (1H, m), 8.01 (1H, d, J=1.8 Hz), 7.83 (1H, d, J=7.8 Hz), 7.72 (1H, d), 7.51 (1H, m), 7.41 (1H, m), 7.33 (1H, s), 7.24 (1H, s), 6.85 (1H, s), 6.75 (1H, d, J=4.3 Hz), 6.59 (1H, d), 3.71 (4H, t, J=4.8 Hz), 3.14 (4H, q, J=4.4 Hz), 2.46 (3H, s). Mass Spectrum (ESI) m/e=455.0 (M+1).

Provenance & Evidence