N,N,N',N'-Tetramethylethylenediamine → HCID 66801722, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-2-(2-chloro-6-fluoro-phenyl)-N-(6-methylpyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine (0.15 mmol, 69 mg), Zn(CN)2 (0.30 mmol, 36 mg), Pd2(dba)3 (0.015 mmol, 13.8 mg), and dppf (0.030 mmol, 16.5 mg) in a 10 mL microwave vial was purged with nitrogen for 5 min. DMF (3 mL) and TMEDA (0.03 mmol; 3.6 mg) were added. The vial was sealed and heated at 140° C. in a microwave reactor for 20 min. The reaction mixture was filtered through celite, washed with EtOAc. Filtrate was concentrated to give a crude product which was purified by reverse phase HPLC to give the title compound as an off-white solid (5.7 mg, 9.6% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.33 (s, 1H), 8.89 (s, 1H), 8.74 (s, 1H), 7.75 (td, J=8.3, 6.2 Hz, 1H), 7.68 (s, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.54 (t, J=8.9 Hz, 1H), 2.43 (s, 3H). LCMS (Method B): RT=4.33 min, m/z 397.1 [M+H+].

Provenance & Evidence