2-Chloro-8-methylquinoline-3-carboxaldehyde → 8-Methyl-2-(1,3-oxazol-2-yl)quinoline-3-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-8-methylquinoline-3-carboxaldehyde (250 mg, 1.21 mmol) in DME (3 mL) was added 2-(tributylstannyl)oxazole (0.31 mL, 1.76 mmol) and Pd(PPh3)4 (70 mg, 0.06 mmol). The reaction mixture was heated in a microwave at 100° C. for 45 minutes. More Pd(PPh3)4 (50 mg, 0.04 mmol) was added to the mixture, which was heated at 100° C. for 2 h. Purification by column chromatography (SiO2, 0-100% EtOAc in heptane) gave the title compound as a cream solid (99 mg, 34%). δH (DMSO-d6) 10.85 (s, 1H), 8.91 (s, 1H), 8.52 (d, J 0.6 Hz, 1H), 8.12 (d, J 8.1 Hz, 1H), 7.86 (d, J 7.0 Hz, 1H), 7.64-7.72 (m, 2H), 2.81 (s, 3H). LCMS (ES+) 239 (M+H)+, RT 3.65 minutes (Method 3).

Provenance & Evidence