Sodium Carbonate → HCID 18407054, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-3-iodo-2-pyridinamine (Description 3, 2.31 g, 9.1 mmol), methyl 5-(4-chlorophenyl)-4-pentynoate (Description 2, 3.03 g, 13.6 mmol), triphenylphosphine (126 mg, 0.48 mmol), lithium chloride (385 mg, 9.1 mmol) and sodium carbonate (4.82, 45.5 mmol) in dimethylformamide (75 mL) was degassed with bubbling nitrogen, then palladium (II) acetate (102 mg, 0.45 mmol) was added and the mixture was stirred at 100° C. for 18 h. The mixture was cooled and further triphenylphosphine (126 mg, 0.48 mmol) and palladium (II) acetate (102 mg, 0.45 mmol) were added. The mixture was degassed with bubbling nitrogen and stirred at 100° C. for 6 h. The mixture was poured into saturated aqueous ammonium chloride and water and extracted with ethyl acetate. The combined organic fractions were washed with water and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (90:10 increasing to 75:25), to give the title compound (530 mg, 17%). 1H NMR (360 MHz, CDCl3) δ 10.90 (1H, br s), 8.10 (1H, d, J 2.2 Hz), 7.92 (1H, d, J 2.2 Hz), 7.60-7.52 (4H, m), 3.64 (3H, s), 3.19 (2H, t, J 7.9 Hz), and 2.65 (2H, t, J 7.9 Hz).

Provenance & Evidence