Potassium Carbonate → HCID 86653031, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-8-methylquinoline-3-carboxaldehyde (258 mg, 1.26 mmol), 3-thiopheneboronic acid (193 mg, 1.51 mmol), K2CO3 (260 mg, 1.88 mmol), palladium(II) acetate (5.6 mg, 0.025 mmol) and triphenylphosphine (26.3 mg, 0.10 mmol) in water (2 mL) was degassed. 1,4-Dioxane (6 mL) was added and the mixture further degassed, then heated at 100° C. for 1 h under microwave irradiation. The reaction mixture was diluted with DCM (30 mL) and water (10 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 10% EtOAc in heptane) gave the title compound (297 mg, 93%) as a colourless crystalline solid. δH (CDCl3) 10.40 (s, 1H), 8.75 (s, 1H), 7.83 (d, J 9 Hz, 1H), 7.60-7.73 (m, 3H), 7.46-7.54 (m, 2H), 2.85 (s, 3H). LCMS (ES+) 254.2 (M+H)+, RT 4.29 minutes (Method 3).

Provenance & Evidence