2-Pyridinecarboxaldehyde → HCID 89601195, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(4-bromo-2,6-dichloro-phenyl)-3-methoxy-cyclopent-2-en-1-one (0.86 g, 2.56 mmol) in anhydrous tetrahydrofuran (17 ml) at 0°C. under an nitrogen atmosphere was added dropwise potassium hexamethyldisilazide (2.81 ml of a 1.0M solution in tetrahydrofuran, 2.81 mmol) over 10 minutes followed by dropwise addition of a solution of pyridine-2-carbaldehyde (0.268 ml, 2.81 mmol) in tetrahydrofuran (1 ml) over 5 minutes. The reaction was stirred at 0°C. for 10 minutes and then allowed to warm to room temperature over 1.5 hours. The reaction was quenched with saturated aqueous NH4Cl (25 ml) and extracted with EtOAc (3×25 ml). The combined organic extracts were washed with brine (15 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography over silica using an EtOAc/isohexane gradient to give the desired product (250 mg, 20%). 1H NMR (400 MHz, CDCl3) δ ppm 8.70 (d, 1H), 7.70 (dd, 1H), 7.55 (s, 2H), 7.45 (d, 1H), 7.40 (s, 1H), 7.25-7.20 (m, 1H), 4.05 (s, 2H), 3.95 (s, 3H).

Provenance & Evidence