反应详情

A suspension of 6-cyano-2-naphthoic acid [J. Med. Chem., 2004, 47, 303-324] (139) (4.62 g, 23.4 mmol) in dry t-BuOH (120 mL) containing powdered molecular sieves (2 g) was treated with Et3N (3.91 mL, 28.1 mmol) and the mixture was stirred at room temperature under N2 for 30 min. DPPA (5.55 mL, 25.8 mmol) was added, and the mixture was stirred at reflux for 6 h, then concentrated to half volume and poured into dilute aqueous NaHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 6-cyano-2-naphthylcarbamate (140) (4.68 g, 74%): mp (MeOH/H2O) 135-136° C.; 1H NMR [(CD3)2SO] δ 9.85 (s, 1H), 8.42 (d, J=0.9 Hz, 1H), 8.23 (d, J=1.0H, 1H), 7.95 (d, J=8.7H, 2H), 7.68 (dd, J=8.5, 1.6 Hz, 1H), 7.64 (dd, J=9.0, 2.0 Hz, 1H), 1.52 (s, 9H). Anal. (C16H16N2O2) C, H, N.

1. additioncontaining
2. stirringthe mixture was stirred
3. temperatureat reflux for 6 h
4. concentrationconcentrated to half volume
5. additionpoured into dilute aqueous NaHCO3
6. customThe resulting solid was purified by chromatography on silica gel
7. washeluting with CH2Cl2