Potassium Carbonate → 6-(4-Carboxyphenyl)-8-(3-cyanophenyl)-1,7-naphthyridine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 6-trifluoromethylsulfonyloxy-8-(3-cyanophenyl)-1,7-napthyridine (2.15 g, 5.67 mmol) in DMF (21.5 ml) is added 4-carboxy-phenylboronic acid (1.13 g, 6.81 mmol), bis(dibenzylidenacetone) palladium (131 mg, 0.23 mmol), triphenylphosphine (95 mg, 0.36 mmol) and aqueous K2CO3 (2N, 17 ml). The reaction mixture is stirred at 80° for 2.5 h. The hot solution is filtered through cellit and the crude product is precipitated by carefully adding water (10 ml) and aqueous HCl (2N, 8 ml). The suspension is filtered and the crude product is stirred in hot THF (30 ml). The cold suspension is filtered again to yield the title compound (1.12 g). M+H=352. Melting point >300°. Retention time HPLC=7.58 min (column: LiChroCart 125-4, Supersphere 60 RP-select B, 400; eluent: acetonitrile-water (0.1% TFA)=45:55; 1 ml/min; detection at 254 nm).

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