Hydrochloric Acid → HCID 24961813, compound

Participants

Reaction Conditions

Reaction Steps

A mixture 3-[7-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenylamine (200 mg, 0.65 mmol), 4-bromopyridine.HCl (130 mg, 0.67 mmol), (±)-Binap (63 mg, 0.1 mmol) and NaOtBu (250 mg, 2.6 mmol) in dry dioxane (3 ml) was deoxygenated by evacuation/refill with N2 (×3). Pd2(dba)3 (30 mg, 0.03 mmol) was added and the mixture was deoxygenated again (×3). The reaction was stirred and heated at 100° C. for 18 hours under N2. The mixture was partitioned between CH2Cl2/H2O, then filtered. The layers were separated and the solid was combined with the organic layer, which was then evaporated. The residue was purified by chromatography on silica followed by preparative HPLC to give the title compound (40 mg, solid). 1H NMR (400 MHz, Me-d3-OD): 8.63 (1H, d), 8.44 (1H, s), 8.22 (2H, d), 7.87-7.79 (4H, m), 7.70 (1H, t), 7.63-7.59 (2H, m), 7.48-7.43 (1H, m), 7.37 (1H, dd), 7.31-7.24 (2H, m), 7.17 (2H, d).

Provenance & Evidence