Tetramethyltin → 3-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

Beteiligte Stoffe

Reaktionsschritte

To a mixture of 1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (500 mg, 1.34 mmol) in N-methylpyrrolidone (NMP) (7 mL) was added SnMe4 (358 mg, 2.0 mmol) and resin-bound-Pd(PPh3)2Cl2 (Sigma-Aldrich) (1-2 mmol/g) (40 mg, ca. 0.03 mmol). The resultant mixture was stirred in a 130° C. oil bath for 3 h. Reaction mixture was filtered and rinsed with NMP (1 mL). Filtrate was poured into water (120 mL) and stirred at room temperature until good precipitate formed. Solid was collected and rinsed with water (100 mL) and then hexanes (50 mL). Solid was dried and purified by silica gel chromatography, eluting with 2-50% EtOAc/hexanes, to provide the title compound 240 mg (0.78 mmol) in 58% yield. 1H NMR (200 MHz) CDCl3, δ in ppm: 11.68 (s, 1H), 8.37 (d, J=9.3 Hz, 1H), 7.48-7.08 (m, 7H), 4.07 (s, 3H), 2.75 (s, 3H).

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