Sodium Carbonate → 4-(4-Formylpyridin-3-yl)-2-methoxybenzonitrile

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Reaction Steps

A mixture of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (259 mg, 1 mmol), 3-bromoisonicotinaldehyde (186 mg, 1.000 mmol), a solution of sodium carbonate (2M in water, 1.000 ml, 2.000 mmol), bis(triphenylphosphine)palladium(11) chloride (17.55 mg, 0.025 mmol) in DMF (6 mL, dry) was heated to 120° C. for 3 hrs. After concentration, the residue was dissolved into CH2Cl2-MeOH and mixed with silica gel and concentrated. After flash column (MeOH—CH2Cl2, v/v, 0.5%-1%) yielded colorless solid (170 mg). 1H NMR (400.3 MHz, CDCl3): δ 3.99 (s, 3H), 6.98 (d, J=1.32 Hz, 1H), 7.05 (dd, J=1.48, 7.8 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.81 (d, J=5 Hz, 1H), 8.81 (s, 1H), 8.90 (d, J=5 Hz, 1H), 10.04 (s, 1H).

Provenance & Evidence