Dichloromethane → 5-(2-Formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)picolinonitrile

Participants

Reaction Conditions

Reaction Steps

Compound 2a (156 mg, 0.500 mmol), 2-cyanopyridine-5-boronic acid pinacol ester (230 mg, 1.00 mmol), and PdCl2(dppf).DCM (40.8 mg, 0.0500 mmol), were placed in an 8 mL vial equipped with a stir bar and then the vial was evacuated and backflushed with Argon gas. Dry DME (4 mL) and 2M Na2CO3 (2 mL) were added sequentially and then the reaction was stirred at 90° C. for 3 h. The reaction was cooled to rt and diluted with DCM (10 mL). The mixture was dried through a Na2SO4 pre-packed cartridge and then the solvent was removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (40-g SiO2 pre-packed column, 0-100% EtOAc/DCM) to afford compound 75a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.08 (s, 1H), 8.93 (s, 1H), 8.17 (s, 1H), 8.02-8.10 (m, 1H), 7.88 (d, J=8.1 Hz, 1H), 7.49 (s, 1H), 4.47 (br. s., 4H), 3.90 (t, J=4.6 Hz, 4H). LCMS calcd for C17H14N6O2: 335.1 (M+H). found: 335.1.

Provenance & Evidence